


Can I Call You Mine?

by justyrae



Category: Julie and The Phantoms (TV 2020)
Genre: Alternate Universe, Alternate Universe - Sugar Daddy, Blow Jobs, Boys Kissing, Hand Jobs, I'll update the tags as I go along right now I can't think of anything, M/M, Reggie blushes all day every day throughout this entire fic, When I Say Alternate Universe I Mean It, everyone in this fic is in their early 20s minus Caleb, everything is consensual and Caleb is NICE, no underage or non-con here, no villains at all!!
Language: English
Status: In-Progress
Published: 2021-02-06
Updated: 2021-03-13
Packaged: 2021-03-18 16:01:30
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 6
Words: 24,781
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29246244
Author URL: https://archiveofourown.org/users/justyrae/pseuds/justyrae
Summary: Reggie and Luke are struggling to pay their bills, so Reggie decides to become a sugar baby. And while he has no real expectations of how this whole thing will go, he gets a lot more than he bargained for when he meets Caleb.
Relationships: Caleb Covington/Reggie Peters
Comments: 70
Kudos: 90





	1. Best Friends

**Author's Note:**

> i honestly have no explanation. i started writing this thinking it would go one way, and then as i was working on it, things changed. and i know this is probably a niche pairing for most but i hope you give it a shot!
> 
> a couple things, before we start - as i mentioned in the tags, everyone (reggie, luke, alex, etc) in this fic is in their early 20s with the exception of caleb, who's probably in his early 40s (idk i didn't think about it that much). there is absolutely no non-consensual anything and before you ask, NO caleb is not a villain. i promise if you give it a chance, you'll probably fall in love with him too. that being said, if this isn't your thing, that's ok! don't worry about it, you don't have to read it!
> 
> i also made a playlist for this fic, you can find the link to it in the end notes. hope you enjoy!

Neither Luke nor Reggie are particularly good with numbers. By extension, they're not the best at handling money. It doesn't really matter a whole lot because neither of them have very much in the way of savings to worry about, but it does start to pose a problem when their bills are due and neither of them have the money to cover them.

That's what leads to Reggie trying to find an alternate way to make money. He tries to pick up extra shifts at the restaurant where he works, but they're few and far between. His tips are decent on weekend nights but if he keeps getting scheduled on the early shifts in the middle of the week, he's not going to be able to make his part of the rent.

Luke isn't much better off with the minimum wage he makes at the convenience store down the street from their apartment, but it doesn't seem like he's as worried about their combined finances as Reggie is. As far as Reggie knows, Luke doesn't spend every break he gets trying to figure out ways to cut costs just to keep the lights on. He's more concerned with how he's going to pay for studio time or the latest recording software instead of their electric bill.

Ever since Luke got his internship at Capitol Records - unpaid, unfortunately - he's been even more singularly focused on his dream. As worried as it makes him, Reggie also can't fault him for it. He's envious of Luke sometimes, for knowing what his true passion in life is. Reggie still hasn't figured out what his is yet, and sometimes it feels like he never will.

In the meantime, he has to keep his head square on his shoulders, not in the clouds. And down here on Earth, Reggie's worried about the electric bill. He's poring over the bill when he's given an idea from the unlikeliest of people: his fellow server, Carrie.

"What're you doing?" she asks, having found Reggie curled up in a corner booth in the back of the restaurant with a pen, paper, and his ancient phone.

"Nothing," Reggie lies as he tries to hide all of his scribbles from her view. But before he can flip the paper over, she's snatched it off the table and examines it.

"What is all of this?" she asks with a snicker. "Have you gone crazy? It's just a bunch of gibberish and numbers."

"It's nothing, it's--" Reggie sighs as he takes the paper back and smoothes it out on the table. "I'm just trying to figure out how I'm going to pay my half of the rent and the utilities and still be able to eat next week."

Carrie frowns. She clearly wasn't expecting such a sob story at eleven in the morning, so she sits down across from Reggie and takes the pen out of his hand. She pulls the paper towards her, finding an empty spot in one corner where she writes down a website.

"What's that?" Reggie asks when she pushes the paper back towards him.

"You don't really think this job pays well enough for a new manicure every two weeks, do you?" Carrie says, wiggling her fingers to show off her rather impressive-looking nails. She shakes her head, giggling as Reggie dutifully types in the website into the browser on his phone.

"Is this--" Reggie lowers his voice, "is this for real?" Carrie nods. "I can't do _this_."

"Why not? You're hot. I bet you'd find someone like that," she says with a snap of her fingers.

"But--" Reggie swallows hard, "isn't it… like, weird?"

Carrie shrugs. "It's not so bad. It pays super well and besides, most of the guys I've seen just want someone to talk to."

"Really?" Reggie sighs. "That's not so bad."

"I'm not saying you _have to_ , I just thought you might wanna give it a try." Carrie shrugs again. "Plus, it's not like we'd be going after the same ones."

"Y-Yeah, true." Reggie nods. "You're probably right."

Carrie waits a beat and then starts to get up. "Well, this has been weird, and my shift's starting soon."

"Wait, Carrie--" Reggie says, catching her before she walks away from the table. "Why do you work here if you're… doing that?"

"Please," she says with a snort of laughter, "if my dad found out how I was _really_ making money, he'd cut off my tuition payments in a heartbeat. This," she gestures around the restaurant, "keeps _that_ from happening."

"Oh. Right, yeah. Of course."

Carrie rolls her eyes. "Later, weirdo."

After she leaves, Reggie looks back down at his phone and stares at the website's front page for a good five minutes before he lets himself scroll any further. He has _no_ idea how he's going to tell Luke about this, or if his best friend will _ever_ let him live it down if it turns out to be a disaster, but he's desperate.

Desperate enough to try and find a sugar daddy.

📸

The website is still kicking around in Reggie's head long after his shift at the restaurant is over. He thought about it while sitting on the bus home, scrolling up and down the homepage on his phone until his battery died. He's needed to replace the phone for a few months now, but that's too far down on his list of priorities to deal with right now.

He thinks about it while he walks the four blocks from the bus stop to his apartment building, trying to think of a way he's going to broach the subject with Luke. They're best friends, they tell each other everything, but how in the _hell_ is he going to tell him that he's seriously considering becoming a sugar baby?

Luke's going to laugh him straight out of the city, Reggie just knows it.

By the time Reggie reaches his building, he's so deep inside his own thoughts that he doesn't even realize he's been greeted by someone coming out of the gate until they shout his name.

"What?!" He flinches, jumping back almost a full foot as he looks at the girl standing before him.

"Are you okay?" Julie gives him a weird look and Reggie laughs awkwardly.

"No, yeah. I'm totally cool." He clears his throat and gestures awkwardly to the sidewalk. "You, umm, off to class?"

"Nah, I had an early one today. Now I'm headed off to work."

"Cool." Reggie nods, feeling a little awkward. He likes Julie and he likes to think that they'd be friends even if her dad wasn't the manager of their apartment building, but then again they've never _really_ hung out together so maybe it's all just in his head.

"Well, I'm gonna go now." Julie laughs as she takes a step further away from him, pushing the gate open so he can go through.

"See you later!" he calls over his shoulder, sighing to himself as he heads down the row of apartments.

Luke's sitting on the pullout couch when Reggie unlocks the door, but he's hunched over their shitty coffee table scribbling away on a piece of paper with a marker.

"Reg! Reggie!" Luke jumps up and brandishes the paper in front of his face, far too energetic for the current time, "look! Look at this!"

"Okay," Reggie says as he takes the paper out of Luke's hands and holds it at a normal distance from his face. "What am I looking at?"

"My ad," Luke says, clicking his tongue as he grins.

"Your… ad."

"I'm gonna give guitar lessons!" He lightly punches Reggie's shoulder. "To help with the rent!"

"You…" Reggie blinks. "When did you decide this?"

"Like, an hour ago?" Luke says as he snatches the paper out of his hands. "What do you think? I was gonna go down to FedEx and make some copies later."

"Can you afford that?"

"Gotta spend money to make money," Luke says before he downs the last of the Red Bull sitting on the coffee table. Reggie sighs as he sets his backpack down, deciding unilaterally that now is _not_ the time to bring up the sugar baby thing.

Maybe tomorrow, after Luke's recovered from the upcoming caffeine crash.

"Bad day?" Luke asks as Reggie sits down on the floor rather than taking the empty seat next to him on the couch.

"Not really," Reggie replies, "just long."

"Make any good tips?" Reggie sighs.

"Not really."

"Then I'd better get moving on these flyers, huh?" Luke says, patting Reggie's knee before he hops up from the couch and moves towards the door. "Wish me luck!"

"Why do you need-- okay." Reggie shakes his head as Luke all but runs out the door, slamming it behind him.

Reggie lets out a long breath and lies down with his back against the floor, staring up at the ceiling. His mind wanders back to the sugar baby website and he groans, reminding himself that he needs to charge his phone. If he's really going to do this then he'll need some way of keeping in contact with his potential… clients.

He grabs Luke's laptop off the kitchen counter, swiping aside the half-empty open bag of Doritos that Luke apparently was eating before. Reggie carries the laptop into the bedroom, plugging in his phone and setting it down on the bedside table before sitting down on the mattress and opening the laptop.

Just to be safe, he opens an incognito tab in the browser before he types in the website address again. Instead of staring at the homepage for another half an hour, he immediately moves the cursor over to the _Make an Account_ link and clicks it.

"This is fine," he murmurs to himself as he starts to type his information in. "Perfectly normal way to spend the afternoon."

📸

Reggie is still on the website by the time Luke comes back from the FedEx print shop. He completed the account registration fairly quickly, but creating his profile was far more extensive than he could've imagined. It took him almost an hour just to pick what photos he was going to show, since he could only have up to five on his profile at the same time. On top of that, there were dozens of questions to show his personality, his likes and dislikes, and what sort of relationship he was looking for.

That had taken Reggie the longest to answer because honestly, he didn't even know.

How was he supposed to know what he wanted when he wasn't even sure if he really wanted to do this? What if he went through all this trouble just to end up hating everything about it?

More than once he wished he had Carrie's number so he could text her and get answers to his questions, or at the very least find out what she'd written on her own profile so he could get _some_ idea of what to put on his.

As it turned out, whatever Reggie thought up seemed to be perfectly fine. No more than ten minutes after finishing his profile, he already has three messages from potential clients.

Reggie discovers the website works more to the benefit of the sugar babies when it comes to maintaining boundaries with their potential clients, which he is so thankful for. The first interaction is more like an email, which gives Reggie access to the client profile and from there he can either delete the request flat out, or accept it and start an instant message chat through the website.

He gets so swept up in chatting with one of his potential clients that he doesn't hear the front door open, nor does he hear Luke calling his name. He does, however, notice when the door to the bedroom opens and suddenly Luke is standing before him with a curious look in his eyes.

"What are you doing on my laptop?" he asks. It's not exactly uncommon for Reggie to use his laptop, but he's more curious about it than he usually would be purely because of the look of absolute panic in Reggie's eyes.

"Nothing!" Reggie says quickly as he slams the laptop shut and clutches it with both hands.

This, of course, was the absolutely wrong move. In a matter of seconds, a smirk spreads across Luke's face and he's up for the challenge that Reggie has unknowingly set. He realizes his mistake a second too late, which earns him a one-way ticket to Luke tackling him down to the mattress as he wrestles away the laptop. Reggie tries to put up a valiant fight, but in the end Luke is victorious and sits on Reggie's back like a throne, pinning him down to the bed as he opens up the laptop to see what Reggie was doing.

"Dude, what is this?" Luke asks as he starts clicking around on the website.

"It's nothing," Reggie grumbles as he tries to shove Luke off of him and get the laptop back. "Don't worry about it."

"Is this what I think it is??" Luke asks, sliding off the bed entirely and turning around to look at Reggie with the laptop still in his hands.

"No!" Reggie tries to snatch the laptop away, but Luke is again too quick.

"Because it _looks_ like--"

"Don't--"

"--you're a sugar baby?!"

Reggie groans loudly. " _No!_ " He hides his face in his hands and Luke flips the screen around.

"No?? Then what's this??"

"I…" Reggie sighs heavily and takes the laptop away from Luke, quickly logging out of the website before he closes the tab. "It's not what you think."

"Is it a joke?" Luke laughs. "The website looked pretty legit, you did a good job!"

"It's not--" Reggie groans. "It's not a joke."

Luke's smile starts to slip. "I don't get it."

"I-- I _am_ a sugar baby. Or, like, I just signed up?" Reggie starts bouncing his leg nervously. "Carrie, that girl I work with at the restaurant, told me about it."

Luke furrows his eyebrows as he sits down at the foot of the bed. "So like… how does it work?"

"I don't really know yet." Reggie tugs at a loose thread on the comforter. "I got a couple messages, but it's not like a _thing_ yet."

"Well, that's good, though, right?" Luke jovially taps his knuckles against Reggie's knee. "Popular already?"

Reggie flushes. "Shut up."

"I'm serious, dude!" Luke crawls up further onto the bed, crouching on his knees as he tries to get Reggie to make eye contact with him. "I mean, like, I don't _really_ know how it works, and like… it does seem a little skeevy."

"I--"

"But!!" Luke says before Reggie can contest his point. "You're not like, selling yourself, right? It doesn't have to be that kinda thing?"

Reggie wants to die. He wants to drop dead right now and get away from this terrible conversation. He really didn't expect Luke to be so cavalier about this whole thing.

"I don't--" Reggie groans. "Do we have to talk about this?"

"I just…" Luke's shoulders slump. "I don't want you to think that you like, have to do this. I know money's tight but…" he sighs, "...you should be doing this because you want to, not because you have to."

"I definitely didn't think this is how my life would turn out," Reggie says with a rueful laugh. "And it's _definitely_ not the kind of career I saw myself in…"

Luke snorts. "I don't know if _career_ is the right word you wanna use for it."

Reggie grabs a pillow and smacks Luke with it. "Shut up."

"Hey!" Luke grabs the pillow and tosses it aside. "I'm just saying. If this is what you wanna do, then I've got your back, bro. Just… don't expect me to start doing it too."

Reggie snorts. "Deal."

Luke holds his fist out and Reggie taps his against it, starting to feel a little better about the whole thing. Luke sighs heavily as he collapses onto the bed on his back, tucking his arms under his head.

"Maybe you'll find a hot dude," he says. "Instead of like, old, crusty ones."

"Dude!" Reggie groans in disgust as Luke cackles. He grabs another pillow and starts wailing on Luke, and it eventually ends in another wrestling match that Reggie inevitably loses. Luke gets him in a headlock and Reggie has to tap out or risk actually passing out.

"Maybe one of them will buy you a laptop," Luke says, a little out of breath from their roughhousing. "And a new phone."

"Maybe," Reggie says with a rough voice. "It'd be nice to have some actual spending money."

"Hey…" Luke reclines on the bed, propping the pillow up under his head, "what would you do with a million dollars?"

Reggie snorts as he lies down next to him. "That's not even that much money anymore."

"Respect the question, dude." Luke shoves him. "C'mon."

"Okay, okay," Reggie sighs, "I'd… I dunno, maybe go to college? Figure out what I wanna do with my life. Like you and your producing. Find my _passion_ , or whatever."

Luke grins. "I bet you could get the money to do that with this sugar baby thing."

Reggie pauses for a moment to consider it. "Yeah," he says softly. "Maybe."


	2. If You Can Afford Me

**Notes for the Chapter:**

> happy chapter two! thank you to everyone who commented on the first chapter <3 i'm glad you guys are giving this a chance! hope you enjoy :)

It hasn't even been a week since Reggie signed up for the website and he's already thinking he's going to delete his account. He's had three coffee dates so far with three different potential clients and every single one has left him feeling overwhelmingly uncomfortable about the whole thing.

He tries talking to Luke about it, but it's just a generally awkward conversation all around. Luke tries to be supportive and tells Reggie to keep at it, but it clearly makes him uncomfortable no matter how hard he tries to make it seem like he's not. Truth be told, the more Reggie thinks about it the more he starts thinking this whole thing was a mistake.

He manages to corner Carrie one afternoon during a shift they overlap on, but even she isn't _that_ much help. All she tells him is that sometimes it takes a while to find a good one.

"That's… not helpful," he grumbles.

Carrie pats his arm. "If it makes you feel any better, there's a good chance you'll find multiple people you like at once." She beams at him. "And then you get even more money!"

"I don't--" Reggie stares blankly at her; he hadn't even _considered_ the fact that he might have to "date" more than one person at a time! "That seems like a lot of work…"

Carrie shrugs and scoffs out a laugh. "It's better than this place, that's for sure."

"Yeah, you're probably right," he mumbles in return.

"Give it a little more time," Carrie tells him. "You never know."

Honestly, Reggie doesn't want to give it more time. He's picked up extra shifts this week which means he has even less time to devote to weird coffee dates where guys almost twice his age try to touch his knee under the table. (The fact that it happened more than once really makes Reggie question his own judgement.)

On his way home after his shift is over, Reggie loads up the website on his phone with the intent to cancel his account. He figures it's better to cut his losses now rather than to keep trying and spend another week going on useless coffee dates and not helping his financial situation at all.

But when he logs in, he's got a new message. Purely out of curiosity he clicks on it, half-expecting it to be another terrible opening line. Instead, he's met with a profile of a man in his early forties who looks like he takes very good care of himself, which is already a plus (but a voice in the back of Reggie's mind reminds him that catfishing is still very much a concern even with the background checks that the website runs).

He learns that the man's name is Caleb, and on the profile he has a link to his Instagram page so Reggie quickly clicks on it to see what he's got on there. At first glance, it's fairly boring. Reggie figures out that Caleb's a professional photographer, as 95% of his Instagram posts seem to be shots from his past jobs. But Reggie keeps scrolling and soon he comes across a candid photo of Caleb at some event where he had to wear a suit and… well.

Caleb looks _good_ in a suit.

Reggie switches back to the website and pulls up the message again, reading it through a second time to make sure he didn't somehow imagine this whole thing.

_Hello, Reggie. I'm not entirely sure what to say that you might not have heard already, but I have a feeling you're as new to this as I am. Just based on your profile, I think you might be exactly what I'm looking for. I hope that's not too forward of me, and I realize that there's probably a lot about you that I can't surmise from an online profile. So, how about we get to know each other?_

If nothing else, Caleb is very well spoken. Reggie feels a little hot under the collar when he thinks about the man he saw in the Instagram photo saying something like this to him in person. In his head, Caleb's got a warm, deep voice that would probably send shivers down his spine.

Reggie accepts the request without another moment of hesitation.

But… then he has to figure out what he's going to say in return. Reggie stares out of the bus window, watching the streets go by as he tries to think of something to say that could even come close to the level of sophistication that Caleb clearly has. After a few minutes of worrying about how not to sound like a total idiot, it hits him.

Caleb clearly already likes Reggie for all the dumb stuff he wrote on his profile. All he has to do is be himself and see where it goes.

_Hi Caleb!_ he writes, trying not to cringe too much already. Should he not use exclamation points? Is that too eager, or too childish? He's already overthinking this too much. _I'd like to get to know you, too. What do you want to know first?_

Reggie gets a reply as he's getting off the bus at his stop, and he can't help but smile.

_How about if you're free for lunch tomorrow?_

"Lunch?" Reggie murmurs aloud as he starts heading down the street towards his apartment complex. "Already moving up in the world."

Luke isn't home when Reggie makes it back to the apartment, which he's more than a little relieved to find out. The laptop is in the kitchen, and Reggie borrows it again to keep chatting with Caleb. He's suggested a couple of places where they could meet for their lunch date tomorrow, and Reggie knows exactly none of them.

_I'm not too picky_ , he writes, _so I'm more than happy to go along with whatever you think is good._

_Well, in that case, how about Cecconi's? It's Italian._

_Sounds great!_ Reggie cringes again, having sent the exclamation point without thinking about it. He googles the restaurant on his phone while Caleb is typing his next message, seeing that it's in West Hollywood. Shit.

"Ooh, that's… far." Reggie bites his lip as he looks at the various bus and subway routes he could take to get there from the Valley, already dreading the cost of the trip.

_I'll make us a reservation. How's 1 o'clock?_

_1 works for me. I'll meet you there._

"Nice," Reggie says under his breath, pumping his fist in the air at his restraint from using an exclamation point. Of course, as soon as he realizes what he just did, a whole new level of shame washes over him and he groans. "I'm hopeless."

_Perfect. Looking forward to meeting you._

Reggie's cheeks turn a little pink. He replies in kind, and then logs off the website and closes the incognito tab on Luke's laptop. Picking up his phone and looking at the directions again, Reggie lets himself feel a little hopeful about this. It already feels like something better than what he experienced with the other potential clients, but he's going to try and not get his hopes up too much.

"It'll be alright," he tells himself as he screenshots the directions and saves them to his phone before closing the map and setting his phone back down on the counter.

With one crisis averted, another soon arises. What the hell is he going to _wear_?

📸

It's pure dumb luck that Luke is still asleep when Reggie leaves for his date. He worked the late shift at the convenience store the night before and has been passed out since he got home at 3am, which means that 11am is the perfect time for Reggie to slip out the front door without Luke ever hearing a footstep.

If he'd been awake there's no chance in Hell that Reggie would've been able to make it out the door without Luke embarrassing him one way or another. The last thing Reggie needs is to show up to his date with a blush in his cheeks already.

What Reggie doesn't count on is running into their friends/neighbors in the courtyard. In fact, he doesn't even see them at first but he hears a sharp whistle behind him and he freezes mid-step, turning around to see Willie and Alex approaching him.

"Look at you!" Alex says as he looks Reggie up and down. "Where are you going looking like that?"

Reggie nervously adjusts his jacket, already half-regretting it in the heat of the late morning sun. It's part of the _look_ , but he's already sweating far too much to be comfortable and at this rate he's going to be a hot mess by the time he makes it to West Hollywood.

"Nowhere," he quickly says, but they don't believe him for a second. Willie loops around him on his skateboard, sending Reggie around in a circle to avoid any jabbing fingers.

"You got a hot date?" Willie asks as he keeps skating around him, laughing jovially as Reggie gets more and more flustered.

"What? No!" Reggie groans. "I mean, yeah, but--"

"What?!" Alex gasps. "Does Luke know about this?"

"What? I don't--" Reggie shakes his head. "This has nothing to do with Luke, what are you even talking about??"

Willie comes to a stop on his skateboard and shares a look with Alex. Reggie stares the both of them down as they have a conversation entirely through their eyes, which just makes Reggie even more nervous.

"Stop that!" he says, "it's not fair. I don't know what you two are saying when you do," he gestures crudely with his fingers, " _that_."

Willie snorts. "You and Luke do it too, y'know."

"We do n--"

"You totally do," Alex interrupts.

"I don't--" Reggie clears his throat and adjusts his jacket again. "I have to go."

"Gonna be late for your date?" Willie calls as Reggie starts to walk away, and he stops abruptly again. Alex covers his mouth to hide his laughter, but it barely works.

"Shut up!" Reggie shouts back.

"So it _is_ a date!" Willie crows triumphantly. "I knew it!"

"Knock 'em dead!" Alex shouts. "You look hot!"

"Shut up!" Reggie repeats, his voice coming out a little hysterical. "I have to go!!"

He storms off, ignoring anything else his friends say as he heads for the gate at the far end of the apartment complex. He's already running behind and he has to jog to the bus stop to ensure he catches the right one.

It takes three different buses and one subway ride to get from the Valley to West Hollywood, but Reggie manages to get to the restaurant with a few minutes to spare. He stands outside the premises for an extra five minutes, trying to catch his breath and hopefully stop sweating so damn much.

He's really regretting the jacket now, but he's come too far to take it off. Hopefully Caleb won't notice the sweat on Reggie's forehead, or if he smells a little. He should've grabbed one of Luke's cologne samples from the bathroom - Reggie has no idea where they even come from but he seems to amass more and more as time goes on - but eventually he has to admit that this is as good as it's going to get, and it's time for him to go inside.

Reggie steps up to the hostess stand and the girl standing behind it smiles at him. He already feels out of place, given that this restaurant is nicer than anywhere he's ever been in, but her smile seems genuine enough that Reggie relaxes a little.

"Do you have a reservation?" she asks, and Reggie balks.

He doesn't know Caleb's last name. He doesn't know if it would be under just his first name, or if he should even give it out.

"I…" he sputters, making various noises of discomfort and unease as he tries to figure out what to say.

The girl's smile wavers a little the longer he goes without giving her a proper answer, but suddenly she brightens up again and Reggie is acutely aware of someone coming up behind him. He goes to move aside, thinking it's someone important or maybe a celebrity and he should absolutely get out of the way, but a gentle yet firm hand takes a hold of his elbow.

Reggie looks to his right and sees Caleb, the absolute spitting image of who he saw in the Instagram post, standing next to him with a winning smile aimed at the hostess.

"He's with me," he says smoothly, and the girl smiles widely at him.

"Right this way, Mr. Covington!" she says, spinning on her heel and leading them to a secluded table towards the back of the restaurant.

Reggie tries not to gawk at his surroundings, but it's incredibly hard not to. Everything in the place looks immaculate and Reggie just hopes he's not leaving dirty footprints on the marble floors.

They're seated at a table with a corner sofa that's covered in velvet, and Reggie gingerly sits down on one side while Caleb takes the other. The girl continues smiling at Caleb as she hands out their menus, and gives Reggie an impressed look before she leaves.

"I hope I didn't embarrass you," Caleb says as he sets his menu down on the table. Reggie swallows hard and mimics the movement, already feeling his cheeks burning a fiery red.

"N-No, I…" Reggie laughs uneasily, "I just realized I didn't know what name to give the waitress and I might've… panicked. A little."

Caleb laughs, not derisively but genuinely amused and even a little fond. The blush in Reggie's cheeks blooms ever redder, and he turns his head in an attempt to hide it.

"This place is… amazing," he says, shaking his head as he glances around again.

"It is," Caleb agrees. "Have you been here before?"

"No," Reggie replies with a laugh, finding it hilarious that Caleb would even _think_ that. "I, uhh, don't spend a lot of time out here."

"Where do you spend your time?" Caleb asks, "if you don't mind me asking."

"Uhh… the Valley?" Reggie laughs again, feeling a little more awkward now. "It's, uhh, well, I'm sure you know."

Reggie balks again at the amused look on Caleb's face, and he tries to backtrack.

"Not that I think you spend a lot of time in the Valley, because I'm sure you don't." He swallows hard. "But, like, everyone sort of knows what it's like there, even if they don't live there. Or never lived there. I just…" Reggie groans. "I'm a little nervous," he admits sheepishly.

"It's all right," Caleb replies. "I'm a little nervous, myself."

Reggie stares at him. "What? Really?"

Caleb shrugs his shoulders and leans back against the velvet couch. "I've actually never done this before, if you can believe that."

"No way," Reggie says, his mouth agape in awe. "But you-- You seem so…"

Caleb chuckles. "I've had the account for a while, but…" he shakes his head slowly, "...I never found anyone who seemed promising." He looks at Reggie and smiles. "Until you."

Reggie's entire _body_ blushes.

"But--" Caleb says, waving his hand a little as he gestures to the menu that Reggie set aside, "--we can save that for after you decide on your lunch. I'd be happy to make some recommendations, if you like."

Reggie laughs nervously as he picks up his menu again, hardly even seeing the words on the paper as he looks down at it. He's never felt this flustered around anyone and he's having a hard time reminding himself that this isn't a _real_ date.

He really doesn't want to get his hopes up, but he has to admit that just five minutes with Caleb has been far more promising than any of the three whole coffee dates ever were. He just also has to keep in mind that this is, first and foremost, a business arrangement - and only if both he and Caleb agree to it. They've still got a long way to go.

📸

By the time lunch is over, Reggie and Caleb have reached an agreement. Caleb ends up making most of the big decisions, or at the very least he seems to know a hell of a lot more about these sorts of arrangements than Reggie does so he knows what to offer. But even so, Reggie still feels like he's got the better end of this deal.

Caleb is _rich_. Like beyond Reggie's wildest dreams _rich_. He figured most of the people on the website were like that but somehow it's still so hard to grasp that this is _actually happening_.

"So," Caleb says as they step out of the restaurant and a black town car pulls up in front of them. "I'll see you on Saturday."

"Yeah," Reggie replies quickly as his cheeks flush. "Saturday," he says calmly.

He steps aside, assuming the car is there for Caleb, but Caleb puts his hand on the small of Reggie's back and gently brings him back towards the door.

"This one's for you," he says as he reaches forward and opens the door. Reggie stares at him open-mouthed, and looks back and forth between him and the car several times before he can figure out anything to say.

"Seriously?"

"Seriously," Caleb says, smiling warmly at him. He steps in a bit closer and puts his mouth to Reggie's ear, "you might want to get used to it."

Just like he thought it might, Caleb's voice in his ear sends a shiver down Reggie's spine.

"O-Okay," Reggie replies as his cheeks go scarlet. Caleb smiles at him again as Reggie climbs into the car, shutting the door behind him.

He manages to give his address to the driver before he collapses against the seat and stifles a scream of joy into the cushion. He rights himself a minute later, exhaling sharply as the car pulls away from the restaurant and out into the street.

By the time the car pulls up in front of the apartment complex, Reggie has mostly calmed down. He has to be back to normal, because he's got to come up with some reasonable excuse as to where he's been for the last five hours so Luke doesn't find out. That's what he _should_ have been doing on the way home instead of replaying the whole lunch date in his head.

Maybe he's overreacting, or putting too much stock in the first meeting going so well, but Reggie actually has hope that everything's going to turn out okay. That for once he and Luke aren't going to have to worry about where their next meal is going to come from or whether the electric company is going to shut off their power in the next couple days.

It's nice to have hope. But it doesn't mean that he won't try to keep a level mind about the whole thing. It's a business arrangement first and foremost, and Reggie has to remember that. He can't go around acting like some lovesick teenager or be too naive to think that this will last forever.

Reggie lets himself into the apartment and finds Luke on the couch watching TV, and everything about his lunch with Caleb immediately goes out the window when he sees what Luke is wearing.

"Seriously?"

Luke snaps his head in Reggie's direction and looks at him with wide eyes. "What?"

Reggie gestures to what Luke's wearing. "I thought we talked about those."

"Yeah, we did." Luke looks down at his overalls and settles back into the couch. "And I _decided_ I'm keeping them."

Reggie groans loudly and then pushes his way past Luke, knocking his feet off of the coffee table, and collapses onto the couch next to him.

"I hate those overalls," he grumbles under his breath.

Luke turns his head towards him and gives him a glare, but then looks him up and down and realizes he's wearing some of his best clothes. "Why are you so dressed up?" Before Reggie can say a word Luke's eyes go wide and he gasps dramatically. "Did you have a date??"

The immediate flush in Reggie's cheeks tells Luke everything he needs to know, but he still wants more.

"So…" he goads Reggie, "what was he like? Was he hot? Was he nice?"

"He was…" Reggie groans helplessly. "... _perfect_."

Luke snorts. "Dude."

"Shut up."

"You've got it bad already?"

" _Shut up_."

"My little baby's all grown up," Luke teases, pinching at Reggie's cheeks despite Reggie slapping his hands away. "Falling in love with weird dudes who pay for dates."

"That's not-- Hey!" Reggie nearly falls off the couch in his attempt to get Luke to stop pinching him, and the only reason he's able to get away is because there's a knock at the apartment door.

Reggie scrambles to his feet, giving Luke a swift kick to his shin as he passes by. He's muttering curses to Reggie's name under his breath as Reggie opens the door, revealing Julie on the other side.

"Julie!" he says loudly, to get Luke to shut up. "Hi!"

"Hi," she replies with a nervous laugh. "I, umm, I'm here for the rent check."

"Oh. _Oh_." Reggie stammers a little as he stumbles into the kitchen to grab their checks off the fridge.

By the time he makes it back to the door, Luke's standing in his place and smirking at Julie.

"Hey, Julie," he says coolly. She rolls her eyes at him.

"Luke. Did you finally lose the last of your shirts?"

"Maybe," he says as he leans against the door. "Like what you see?"

Julie makes a show of looking him up and down, and then rolls her eyes again and looks at Reggie instead. "Has he always been like this?"

"Pretty much," Reggie agrees, much to Luke's chagrin. "I told him those overalls were terrible, but he won't listen to me."

"They're not that bad!"

"You should listen to him," Julie says as she takes the checks from Reggie. "He's got style. You…" she waves her hand around at Luke and snickers, "...do not."

"I do too," Luke replies grumpily.

Julie shakes her head and waves to Reggie before she bounces down the steps leading away from their front door. Luke frowns as he closes the door, glaring at Reggie like it's somehow his fault he's mad. He shoves him a little on his way back to the couch, and Reggie just stares at him.

"What did _I_ do?" he asks rhetorically, knowing full well he's definitely not getting an answer.

**Notes for the Chapter:**

> see you next week!


	3. It's Gonna Be Me

**Notes for the Chapter:**

> yay chapter three! this is the longest chapter for this fic that i've written to date (i've only got two chapters left to write, eee!) so i hope you guys enjoy it.

Reggie's starting to get nervous about his second date with Caleb. They've been texting a little since their initial date, and he knows that Caleb's going to give him a copy of their agreement in writing on Saturday. Even though they went over everything pretty extensively during their lunch, Reggie still feels weird about having the terms laid out on paper.

It makes it feel more real, but it also gives this whole arrangement a cold, business-like feeling that Reggie isn't sure if he can come to accept. He keeps having to remind himself that this _is_ business; that Caleb is basically paying him for goods and services, and that the written agreement is proof of that.

Maybe it won't be as weird as he thinks it will be. But there's only one way to find out, and somehow Reggie has to try and stay calm until Saturday night rolls around.

On top of his nerves about the second date, Reggie can't stop thinking about something that Luke said to him a few days ago, later in the evening after Reggie had come back from his first date with Caleb. He'd stopped making jokes after Julie left, instead turning more serious than Reggie had seen him be in a while.

"You're gonna be safe, right?"

Reggie balked at the question at first, his mind immediately going somewhere that Luke _clearly_ hadn't intended.

"Not like that!" he said harshly, smacking the back of Reggie's head. "Don't be gross!"

"I'm not--"

"I meant like, you're gonna vet this guy, right?" Luke frowned a little. "Like, just because he's rich and seems like a nice guy doesn't mean he can't be a creep."

"I don't know how I'd even begin to _vet_ him," Reggie replied with a heavy sigh. "But like… if I start feeling weird around him, I'll call the whole thing off. It shouldn't be that hard, right?"

Luke just shrugged. "I dunno, man. I just want you to be careful."

The conversation sticks in Reggie's head all week, even though he picks up a couple extra shifts at the restaurant through the rest of the week to try and help distract him a little. He even manages to get one for Saturday morning, though he's definitely distracted through most of it.

When Reggie's Saturday shift ends, he realizes that he doesn't want to go home. Even if Luke's not there, just being in their apartment is gonna remind him of their conversation. If he sits in the empty apartment until it's time for his date with Caleb, he'll make himself crazy.

Reggie's been off the clock for over an hour when Carrie finds him sitting outside the restaurant. She almost misses him because she's intending to go in the opposite direction, but when she sees him sitting down on the edge of the sidewalk she decides she can't just _leave_ him there.

He doesn't see her approach, he doesn't even know she's there until she gently knocks the top of her foot against his thigh. When Reggie looks up at her she's busy texting on her phone, but within a few seconds she puts her phone away and gives him a sympathetic smile.

"What are you still doing here?" she asks as she extends a hand to help him up.

Reggie sighs heavily as he takes her hand. "Don't really wanna go home," he admits miserably.

"How come?" Carrie asks.

"I, umm…" Reggie sighs. "I have a date tonight and I'm kinda freaking out about it." He hangs his head. "And Luke - my roommate - said something the other day that I can't stop thinking about and it's just… it's all a lot, you know?"

"Oh." She clicks her tongue and gives him a sympathetic smile. "Do you wanna grab a coffee and talk about it?"

Reggie blinks. "Really?"

"Yeah, I mean…" Carrie shrugs. "No offense, but you look really miserable."

"Thank you?"

"I just mean, you look like you could use somebody to talk to." She shrugs again and her smile turns less sympathetic and more genuine. "And I know we're not close or anything, but maybe talking to someone who's removed from the situation might help."

"Yeah, I…" Reggie laughs softly. "I think that might, actually."

Carrie smiles wider as she hooks her arm through Reggie's and leads him down the sidewalk. She pulls out her phone a moment later, quickly typing out another text as they go.

"I'm not keeping you from someone, am I?" Reggie asks. "Because I can--"

"It's okay, Reggie," Carrie says as she puts her phone back in her bag. "I just told my girlfriend to meet us at the coffee shop I'm taking you to."

"Oh, okay." A moment goes by and then Reggie balks. "Wait, girlfriend?! You have a girlfriend?!"

Carrie laughs. "We're talking about you, not me." She pats his arm. "One thing at a time."

When they get to the coffee shop Carrie insists on paying for Reggie's order even though he tries not to let her. She smacks his hand away every time he tries to hand his card to the barista and eventually has to body check him to the side to get him to stop.

"My treat," she says definitively, turning back to the barista with a winning smile as she hands over her card. Reggie quietly accepts defeat and gratefully takes his coffee.

"You didn't have to do that," he says when they pick a table and sit down.

"What's done is done," Carrie says as she flips her hair over her shoulder and props her chin up in the palm of her hand. "Now, spill."

Reggie sighs heavily and stares down at his coffee. "I don't even know where to start."

"Your date," Carrie says as she rolls her eyes. "Duh. Do you like the guy?" She drops her voice and cups her hand around her mouth. "Is it a guy? Or a they?"

"That's not--" Reggie groans and Carrie shrugs her shoulders.

"I didn't want to _assume_."

"No, it's…" Reggie drops his voice down to a whisper. "I signed up for that website you gave me. The sugar baby thing?"

"You did?" Carrie gasps excitedly. "Is this a date--"

"Yes!" Reggie hisses, frantically looking around as if anyone in the coffee shop is actually paying attention to their conversation.

Carrie sighs patiently. "It's perfectly normal to be nervous for a date, especially in our line of work." She winks at Reggie and his cheeks go red. "But you said your roommate…"

"Luke."

" _Luke_ , right. He said something to you? Was it about the sug--"

"Yes," Reggie interrupts, and Carrie rolls her eyes at his paranoia. "Don't say it so loud," he begs.

"Okay, okay," Carrie says before she takes a sip of her coffee. Reggie does the same, wincing when it hits his tongue because it's still just a little too hot for his liking. "What did he say?"

"He just… he said that I should be careful. That this guy could seem nice and great but underneath he could be a total creep."

Carrie snorts. "Well, he's right. You _do_ need to be careful."

Reggie groans miserably. "How am I supposed to find out if the guy's a creep unless I get to know him better?"

Carrie shrugs. "Perils of the job. You just have to trust your gut, you know? You'll know if he's a creep. Most guys can't hide that kind of thing for long." She smiles at him. "No offense."

"I'm-- _hey_." Carrie snickers.

"I'm kidding. You're not a creep." She pats his hand. "And it's nice that your roommate is looking out for you." She takes another sip of her coffee and gives Reggie a look that he can't identify. "You sure he's not jealous?"

Reggie balks at the question. "What? No! Luke's not-- We're not like that!"

"Just asking!" Carrie laughs softly as she sets down her coffee. "I don't know the _intimate_ details of your friendship."

"We're _just_ friends." Reggie makes a sweeping gesture with his hand. "Luke's very much into girls."

Carrie's smile softens. "Okay," she says. "He and I have that in common."

"Hey," Reggie says suddenly, having just remembered something, "you have a girlfriend."

"Yeah?" Carrie snorts. "But we're not talking about me."

"No, I mean… you have a girlfriend, but you're a sugar baby? How does that work?"

Carrie laughs. "Remember what I said when I first told you about this whole thing? That most of the guys I'd met just wanted someone to talk to?"

"Yeah…" Reggie gives her a confused look. "Wait."

Carrie laughs again. "It's about companionship more than anything else. I have my own boundaries and if the clients I work with can't stick to them, then I don't work with them anymore. It's as simple as that."

"And your girlfriend is okay with that? About you seeing…"

"Guys?" Carrie snorts. "Just because I'm bi doesn't mean I'm going to cheat, you know."

"No, I didn't--" Reggie splutters as he tries to apologize, but Carrie grins at him.

"Oh my god, chill! I'm _kidding_." She rolls her eyes and pats his hand. "And yes, she's okay with it. Flynn and I don't keep secrets from each other."

"Are you talking shit about me?"

Reggie's head snaps up as a girl approaches their table, and he stares wide-eyed as she pulls up a chair and sits down next to Carrie. They quickly kiss each other hello and Carrie links their hands together, smiling warmly at her girlfriend.

"I'm always talking shit about you," she says teasingly, and Flynn rolls her eyes and flicks the tip of Carrie's nose.

"I'm Flynn," she says as she holds out her other hand to Reggie. "And you must be Reggie."

"Th-That's me," he says as he takes her hand and shakes it. "Carrie's told you about me?"

"She said you were having a crisis," Flynn explains, "and I know you work together. As for your life story, though…" she looks at Carrie and shakes her head, "...she's not very helpful with that."

"Well, now that you're here, you can interrogate him all you like," Carrie replies. "I was just telling him about our agreement about my _other_ job."

"Oh?" Flynn cocks her head to the side and looks back at Reggie. "Are you a su--"

"Yes," Reggie says quickly, and Flynn bites back a laugh.

"Aww, he's embarrassed. That's cute."

"I'm not--" Reggie blushes and ducks his head. "Okay, maybe a little."

"No need," Flynn says as she pats his hand in the same way Carrie does. "I know _all_ about that stuff. It's not a bad gig, if you ask me."

"That's what I keep trying to tell him," Carrie says with a sigh. "He's nervous because he has a second date tonight and his roommate got in his head about it."

"That's not--" Reggie groans.

"Ooh," Flynn says with a frown, "he doesn't get it?"

"No! That's just it - he's super supportive!" Reggie sighs.

"That's a good thing!" Flynn looks at Carrie. "Right?"

"He told him to be wary," Carrie explains, "and now poor Reggie's all in a tizzy."

" _Oh_ ," Flynn says knowingly. Reggie puts his head down on the table and groans. He's going to be embarrassed for the rest of his life. He looks up when Flynn puts her hand on top of his and says, in a very serious tone, "just remember. Your body, your choice."

Carrie tries and fails to hide her burst of laughter and Reggie's cheeks feel like they're on fire.

"Thanks?" he says as Carrie tries to stop laughing by taking another sip of her coffee.

"It's a good rule of thumb," Flynn says, patting Reggie's hand twice before she pulls hers back. "Especially if your whole _arrangement_ involves--"

Reggie balks. "Uhh… well, I'm not… I haven't--" He clears his throat. "It's just been one date. N-Nothing like that, yet."

"Yet?" Carrie raises an eyebrow.

"I don't--" Reggie groans and puts his head down on the table as the girls giggle. "That's not what I meant."

"I like him," Flynn declares. "Can we keep him?"

"Only if you stop _teasing_ him," Carrie says as she gently ruffles Reggie's hair. "It's gonna be okay, Reggie."

He slowly lifts his head. "It is?"

"Scout's honor," Carrie replies, holding up three fingers.

"You were never a girl scout," Flynn says, rolling her eyes as she bats Carrie's hand down.

"I could've been!"

"Anyway," Flynn says pointedly, turning her attention back to Reggie. "Tell us more about this guy you've got a date with. When are you seeing him again?"

"Tonight," Reggie admits nervously. Both girls gasp and squeal in excitement.

"Where's he taking you?" Carrie asks.

"Is that what you're wearing?" Flynn asks.

"I don't--" Reggie gulps. "Yes?"

"Don't worry," Carrie says as she takes his hand and squeezes it. "We've got this."

📸

Instead of going back to his and Luke's apartment, Carrie and Flynn decide to take Reggie on a little shopping excursion. Partially to try and give him more confidence about his date tonight, but mostly because Reggie admitted that he doesn't have a lot of nice clothing. Carrie is _convinced_ that Caleb is going to take Reggie somewhere really nice for dinner, even if Reggie isn't sure where that place is, which means he has to dress for the occasion!

"How am I supposed to dress for it when I don't even know what _it_ is?" Reggie asks as Carrie and Flynn drag him around the mall, each one having hooked her arm through Reggie's so he won't get away.

"Just dress hot, duh." Flynn rolls her eyes. "Hot is always in fashion."

"It's true," Carrie agrees. "We'll find you a good pair of tailored slacks and a button-up shirt, maybe even a jacket."

"Oh, with a pop of color," Flynn adds. "Either with the shirt or like a pocket square."

They pause for a moment and Flynn makes a face.

"Nah, a pocket square is too much. A good floral print, though…" Her eyes glaze over a little and she smiles. "Subtle, but eye-catching. Yes!"

"I told you she was good at this," Carrie stage-whispers to Reggie.

The girls split up once they make it into a department store that is _way_ out of Reggie's price range. He keeps close but looks around nervously, trying to check a few price tags without drawing too much attention to himself. He balks when he sees a plain t-shirt for almost $100, and balks again when the girls return with armfuls of potential clothes for him.

"I don't-- I can't--" Reggie lowers his voice, "this stuff is way too fancy! I can't afford this!"

"Yes, you can," Carrie says as she pushes her armful of clothes into Reggie's arms. "Or, well, you'll be able to after your first _paycheck_." She winks at him and Reggie flushes. "I'll cover it for today, and you can just pay me back later."

"Are you sure?" Reggie says, grunting when Flynn unloads her findings into his arms too.

"This is for your own good, Reggie." Flynn pinches his cheek. "Now come on, to the dressing room!"

True to their word, Carrie and Flynn's clothing choices turn out to be perfect. It's very clear that he's not the only one who thinks he looks good because when he comes out of the dressing room in the full outfit, Carrie wolf-whistles loudly as Flynn whoops.

"Yes!" she cheers. "You're hot!"

Carrie cackles beside her as Reggie covers his face to hide his red cheeks, but he dutifully spins around in a slow circle to give them the full effect of his outfit.

"We do good work," Carrie says approvingly.

"We totally do." Flynn grins at Reggie. "You should make us your personal shoppers from now on."

"I'll get right on that," Reggie replies sarcastically.

"See that you do."

They part ways shortly after Carrie pays for Reggie's new outfit, and he swears he'll pay her back just as soon as he can. She smiles as she gives him a hug, patting him on the shoulder as she tells him she knows he's good for it. Flynn surprises Reggie with a hug as well, and laughs at the look on his face.

"We're friends now! Friends hug!"

"Okay!" Reggie says, grunting softly when Flynn hugs him again before taking Carrie's arm in her own and they both turn away from Reggie, leaving him alone on the sidewalk.

Reggie has barely half an hour to get ready after he gets back to the apartment, which is only aided by the fact that he doesn't have to agonize over an outfit. It's also a miracle that Luke isn't around to tease him about the effort he's putting into this date. Reggie's never dated anyone as long as he and Luke have lived together and if it's this bad when he's being a sugar baby, he definitely can _never_ bring home a real boyfriend.

There's a text from Caleb on his phone when he gets out of the shower, telling him that a car will be outside his apartment complex in fifteen minutes. Reggie tries not to panic, because it's still plenty of time to get dressed and restyle his hair, but his heart beats a little faster every time he checks the time.

With hardly a minute to spare, Reggie steps out of the apartment in his new outfit and freshly styled hair, taking a second to breathe in deeply before he locks the door behind him. He walks towards the gate at the front of the apartment complex, hoping and praying that he doesn't run into anyone he knows.

Reggie exits the courtyard through the security gate when he sees the black town car approach, but the rear door opens right as the car comes to a stop at the curb. Caleb steps out a moment later and takes Reggie entirely by surprise.

"You're--" He blinks several times in quick succession and tries not to look as bewildered as he feels. "I thought I was meeting you there?"

"I thought you might like the company," Caleb says warmly. "Wouldn't want you to get lonely if there's traffic."

Reggie laughs. "There's always traffic."

"Exactly," Caleb says as he puts his hand on the small of Reggie's back and leads him to the door. "You look incredible, by the way."

"Th-Thank you." Reggie's cheeks burn as he slides into the car with Caleb right behind him.

He finds a manila envelope on the seat and as he goes to hand it to Caleb, he's met with the wave of Caleb's hand.

"That's for you," Caleb says as he shuts the door behind him, signaling the driver to pull into the road. "It's a copy of the agreement I had drawn up for the two of us."

" _Oh_." Reggie stares down at the envelope and takes a deep breath. "Should I read it now?"

"If you'd like. There's no rush for you to sign it, I want to make sure you have time to read the whole thing as many times as you'd like."

"I'm sure it's fine," Reggie says, "you seemed like you knew what you were talking about, and I wouldn't--"

"You should read it," Caleb interrupts firmly. "You should never sign something you haven't read through."

Reggie clears his throat. "Right. I… I knew that."

Caleb smiles at him. "It's alright, Reggie. I'm not trying to take advantage of you."

"No, I didn't-- I know that, I just--"

Reggie pauses when Caleb puts his hand on his knee, sending a flood of warmth up his thigh. He looks over at Caleb, who's looking back at him with a warm smile and a look of genuine concern.

"It's important," he says, "that you know what you're getting into. That we both do. And if there's anything you don't agree with or want changed, I want you to feel comfortable enough to tell me."

"Okay," Reggie replies, swallowing hard. "I'll, umm, take a look now."

Caleb takes his hand away and Reggie closes his eyes for a moment. It's easier for him to think without Caleb touching him, but part of him wishes that Caleb hadn't pulled away. He lets out a long breath as he opens the envelope and pulls out the contact, finding it much shorter than he thought it might be.

It lays out every single thing they discussed over lunch, only in slightly more legal terms. Some of it is a bit difficult for Reggie to understand on the first read, which leads to him reading the same sentences over and over a few times before he truly gets their meaning.

Next to him, Caleb stays silent. On occasion Reggie can feel Caleb looking at him, but he tries to ignore it and concentrate on the contract as best he can.

His eyes go wide when he looks at the amount he'll be getting as a weekly allowance. Caleb had only briefly mentioned it before, and Reggie hadn't known how or if he should negotiate for more. But now that he was looking at it - $2,000 every _week_?! - he felt a little guilty. Like maybe he was the one taking advantage, not the other way around.

But the real kicker is further down in the contract, and Reggie chokes on air when he reads the clause regarding any _changes_ in the nature of their relationship. He reads the lines nearly half a dozen times before he realizes that yes, it is saying exactly what he thinks it's saying.

If their relationship turns sexual, Reggie will get paid _even more_.

"Caleb, this… this is too much."

"What is?"

Reggie turns the contract towards him and points to the clause he'd just read. For a moment, Caleb actually looks _embarrassed_.

"Ah. Yes, about that." He clears his throat and for a moment, Reggie feels really nervous. "I wasn't sure how to include… that."

"I just… you don't have to--"

"I know we're both new to this," Caleb says, "but I thought it was better to get that out in the open sooner rather than later. I don't want you to be caught off guard, or to be put in a situation where you don't feel comfortable."

Reggie looks down at the contract and flips back to the first page before he sets it aside. "Caleb, can I ask you something?"

"Of course."

"You're… well," Reggie blushes a little more as he speaks, but he's determined to get his thoughts out, "you're successful and super hot, like," he gestures wildly to Caleb's whole body, "just… _wow_. So… why this? Why not actually… date someone?"

Caleb laughs, clicking his tongue as he taps the side of his jaw with his thumb.

"I thought you might ask that."

"Should I-- You don't have to--"

"No, I think it's an honest question, and it deserves an honest answer." Caleb sighs softly. "With money comes a number of things. Some good, some bad. And a lot of the bad usually stems from relationships, both business and personal. Add in a certain level of fame and… well. People become less like people and more like vultures."

"Oh." Reggie's heart sinks a little. If this is how Caleb feels about people, then what is Reggie doing here at all? Isn't he a vulture, so to speak?

"But with something like this," Caleb continues, "at least we're both on the same page. There's no deceit, there's no pressure. It's just two consenting adults in agreement and that," he gestures to the contract, "means that we stick to it. And when it no longer serves its purpose, it can end. Does that make sense?"

"I… I think so?"

Caleb chuckles. "I'm not so naive as to think that anyone on that website in your position is in it for anything other than money."

Reggie swallows hard. Hearing it out loud from Caleb somehow sounds worse than everything that Luke has said already. He sinks in his seat a little, half-wishing he had the courage to ask the car to pull over. Maybe this was a terrible idea.

"But," Caleb says as he leans over and puts his hand back on Reggie's knee, "seeing as how I have more money than one man could ever need, and even though we've only spent a few hours together, I feel a connection to you that I haven't felt in a long time. And I'd like to help you, if you'll let me."

Reggie looks at Caleb and offers him a smile, though he still feels overwhelmingly guilty.

"Are you sure? I'm not taking advantage of you?"

Caleb laughs at that, louder and more humorous than before. "It's possible, but I think I'd like you to anyway."

Reggie blushes, ducking his head as he puts his hand on top of Caleb's.

"Besides," Caleb says as he leans over, sliding a bit closer to Reggie, "I'm fully going to take advantage when it comes to showing you off. You really do look incredible."

Reggie is still blushing a deep red by the time they reach the restaurant. He keeps his head down as they go towards the entrance, partially due to the number of paparazzi outside on the sidewalk. Caleb gallantly creates a path through them, keeping Reggie close as they make their way inside.

"Are you famous?" Reggie asks softly once they're inside, and Caleb chuckles.

"Not enough to warrant those vultures," he replies. "But, in some circles, I suppose I am a little famous."

"Wow," Reggie says, the awe coming through full force. "That's cool."

Caleb smiles at him. "If you say so."

He turns to the hostess and gives his name for the reservation, and within a few minutes they're seated at a table in a far corner of the restaurant, just like they had been for their lunch date at Cecconi's.

Reggie looks at the menu more closely than he had at their previous lunch, and he balks when he looks at some of the prices. He looks up and over at Caleb, the words _I can't afford this_ on the tip of his tongue and then he remembers. He's not the one paying for it.

"Something wrong?" Caleb asks when he notices Reggie looking.

"No," he answers quickly, "I just… I don't eat sushi often." He gulps. "Got any recommendations?"

Caleb points out a few things that he likes on the menu, and helpfully explains some of the items that Reggie has never heard of before. He tries not to keep track of the bill that they're racking up as Caleb orders for the both of them, but all Reggie can think about is how he could pay off several of his bills with the money Caleb is spending on this meal.

And then he remembers that he'll be getting his first _paycheck_ soon, and he shifts uncomfortably in his seat. He just keeps having to tell himself that this is okay, this is the way this sort of thing works, and he's not taking advantage of Caleb.

He relaxes as the evening progresses, thoroughly enjoying Caleb's company just as Caleb enjoys his. Reggie starts to forget he had any reservations at all. He hardly spares a thought to anything outside of what's right in front of him in the moment.

Especially when Caleb offers him food directly from his own hand. Reggie accepts it without a second thought, but when Caleb's thumb brushes against his bottom lip it sends a spark across Reggie's skin and suddenly he's _very_ aware of how close they are to each other. He notices the way the candlelight reflects in Caleb's eyes and sparkles every time he looks at him.

That feeling stays deep in Reggie's chest through the end of the meal, and even when they climb back into the car at the end of the night. Reggie finds his copy of their agreement lying on the seat right where he left it, and when Caleb turns to look at him he asks for a pen.

Caleb smiles as he reaches into his pocket, pulls out a pen, and hands it to Reggie. He passes it back along with the agreement a moment later after he's signed it and Caleb takes it.

"No notes?" he asks. Reggie shakes his head.

"I think you covered everything," he replies.

"In that case," Caleb says as he sets the papers aside, "how would you feel about an afternoon date tomorrow?"

Reggie's face splits into a smile and he laughs bashfully. "Sounds great."

📸

When Reggie wakes up the following morning, the apartment smells weird. Not weird in a bad way, but still weird. He ventures out of his room and finds Luke in the kitchen making breakfast. It solves the mystery of the weird smell, but now Reggie's suspicious for a different reason.

Luke never makes breakfast. But here he is, making eggs, and it seems like he's planning on sharing them with Reggie.

"Good morning," he says with a sly smile as Reggie steps further into the kitchen.

"M-Morning," Reggie replies warily. "What's going on?"

"What?" Luke gestures down at the pan with the spatula in his hand. "I'm making breakfast!"

"I see that. Why are you--" Reggie suddenly catches a glimpse of his contract sitting on the counter between them and his face goes pale.

He totally forgot that he'd left it in the kitchen last night after he got home from his date with Caleb. There's no way Luke wouldn't have read it, especially when Reggie was stupid enough to leave it lying around. He practically gave it to Luke himself.

"Hungry?" Luke asks, his smile growing wider when Reggie looks at him again.

"Mm-hmm," Reggie squeaks out.

Luke serves him up a plate of slightly runny scrambled eggs with a side of toast that Reggie is pleasantly surprised to find not burnt. He waits for Reggie to take the first bite, silently goading him into it with a charming smile.

"How is it?" he asks after Reggie's swallowed.

"Good," he answers honestly. He was half-expecting the eggs to be disgusting, but they're not bad.

"Good!" Luke replies happily as he takes a large bite out of one of his own pieces of toast. Reggie chuckles nervously, continuing to eat his breakfast while keeping a wary eye on Luke.

He's lulled into a false sense of security when Luke stays quiet as he eats. Reggie almost forgets what he was worried about, until Luke pushes his plate to the side and leans towards him, resting his elbows on the counter between them.

"So, _Reginald_ ," he starts, and Reggie's stomach drops. "About this contract of yours--"

Reggie groans. "I knew you read it! I knew it!"

"Maybe you shouldn't leave stuff lying around if you don't want me reading it," Luke counters, snatching up the contract before Reggie can grab it.

Another rookie mistake, leaving it out a second time.

"Now," Luke says succinctly, licking the pad of his thumb as he pretends to flip through the pages of the contract, "according to page--"

"Please," Reggie begs, hiding his face in his hands as Luke goes on, "don't--"

"--regarding the _change_ in the nature of your _relationship_ ," Luke says, putting emphasis on practically every other word just to make Reggie squirm. "I think we need to have a talk about this, young man."

"We really don't."

"Oh, yes we do. Because you see, since I'm the elder around here--"

"By three months!" Reggie groans. "Three months!!"

"I think it's time we had The Talk."

"No." Reggie shakes his head violently. "Nope. Absolutely not. This is not happening."

Luke lasts for another ten seconds before he bursts into uproarious laughter and Reggie crosses his arms, entirely unimpressed by the situation. He waits for Luke to stop laughing, which takes even longer than he thought it would, frowning at him the whole time.

"Are you done?" he asks.

"Yeah," Luke wheezes. "Couldn't resist." He holds the contract out for Reggie to take, snickering when he snatches it away. "I did read it over, though. Seems legit."

"Thank you," Reggie says flatly. "So glad you approve."

"Hey," Luke says, his voice softening. "I'm serious."

Reggie looks at him and Luke actually _does_ look serious. All the irritation he felt a moment ago melts away in a second, and Reggie sighs.

"If you think this Caleb guy is good, then I'm happy for you." Luke smiles at him. "And, y'know, if you wanna buy me something _really_ cool for being so supportive, then I--"

Reggie rolls his eyes and grabs the closest thing (which happens to be the spatula Luke was cooking with) and chucks it in Luke's direction.

"Hey!" he yelps as he dodges it. "Rude! I just made you breakfast!"

"Thank you for the breakfast," Reggie says as he starts walking away. "You're a dick!"

"See if I ever make you eggs again!" Luke calls after him as Reggie disappears into his room.

He closes the door behind him and thumbs through his contract again. Goosebumps prick up on his arms as he thinks about the fact that they have another date today, so soon after their date the night before.

Reggie tries to get a grip on himself. He and Caleb are part of a business arrangement, after all. He shouldn't go all mushy every time he thinks about Caleb, or else this is probably going to blow up in his face very quickly.

"I can do this," he tells himself as he sets the contract down on his bedside table before turning towards his closet. "I can do this," he repeats as he starts getting dressed.

Maybe if he says it often enough, he'll start to believe it.

**Notes for the Chapter:**

> see ya next saturday!


	4. The Beach

**Notes for the Chapter:**

> time for some bff shenanigans followed by the best dinner date ever. enjoy!

The following day is a rarity; neither Luke nor Reggie have to work. Usually Luke has back-to-back shifts between his internship and the convenience store, but every once in a great while he has a day where he doesn't have to be at either. It's Reggie's day off from the restaurant, and his next date with Caleb isn't for another three days.

Luke wants to take full advantage by spending _all day_ at the beach.

This, of course, means they need to con Alex and Willie into coming along because Alex has a car. The moment Willie opens the door to their apartment and sees Luke with a bag under his arm with a towel sticking out of it, he knows exactly what they're here for.

"You guys are lucky," he says after he calls Alex over, "we don't have anything planned today."

"Perfect!" Luke says, grinning widely as Alex comes to the door. "Grab your keys!"

"Why…?"

"Because if we ask you really nicely, you'll come to Venice with us?" Reggie asks, smiling to try and sweeten the deal. Alex sighs heavily, rolling his eyes even as Willie tosses his arm over his shoulder.

"C'mon," he says as he jostles his boyfriend. "It'll be fun."

Alex grumbles under his breath until Willie leans over and whispers something in his ear, and then suddenly Alex changes his tune.

"Give us ten minutes," he says shortly as he slams the door in their faces.

"I think that went well," Luke says as he spins on his heel and starts heading for the parking lot at the back of the apartment complex. Reggie follows.

_Twenty_ minutes later, Alex and Willie meet them at Alex's car. Neither Reggie nor Luke make any comments (out loud, anyway) as they all pile in. They've been driving for about ten minutes when Reggie's phone buzzes with a text and he pulls it out of his pocket.

Luke turns his head, immediately spotting that Reggie has a new phone. He gasps in surprise, totally over-the-top, and Reggie tries to hush him before Alex and Willie turn around to see what the fuss is about.

"Shut up," he hisses.

"Where'd you get the phone?" Luke whispers as he wiggles his eyebrows. "Did _Caleb_ \--"

"Yes, _shut up_!" Reggie hisses again, slapping Luke in the chest.

"You little--" Luke launches a counter-attack, causing the two of them to have a scuffle in the backseat.

"Hey! Hey!" Alex snaps from the driver's seat. "Don't make me turn this car around!"

Willie cackles from the front passenger seat and Luke and Reggie immediately separate.

"Sorry, Mom," Luke says as he crosses his arms. "Reggie started it."

"I did not!" Reggie glares at Luke, who smirks back at him. "Jerk," Reggie mumbles as he _finally_ checks the text on his phone.

Caleb had surprised him with it when they met up for their date the day before. Reggie thought that would be the only gift he received that day, but he was wrong. After they'd gotten his new phone activated, Caleb took him on a shopping spree on _Rodeo Drive_.

Reggie has no idea how much money Caleb spent on him yesterday, but he's sure it was more than he could make in six months working at the restaurant.

_Good morning_ , the text reads. It's from Caleb. _I hope you slept well last night_.

Reggie sneaks a look at Luke, who's finally turned his attention towards the window instead of trying to peek over Reggie's shoulder. He turns back to his phone and smiles at the screen as he types out his response.

_I did! I'm headed to the beach with some friends right now, what are you doing?_

The reply comes through before Reggie even has a chance to put his phone away.

_Something decidedly less fun than spending the day at the beach. Make sure you wear sunscreen._

Reggie flushes a little as he types back, _I will! My friend Alex always makes sure we all do._

He presses send, and then, after a moment of thought he decides to send another message. _I can send you some photos, if you want? To make your boring day a bit more fun?_

It's not meant to be dirty, not _really._ Reggie knows it could probably be construed that way but honestly, he was thinking more about sending photos of the ocean more than anything else. He starts second-guessing himself when Caleb doesn't answer right away, having a minor meltdown in the backseat as quietly as possible.

But then Caleb texts back. _I'd like that_ , it says, and Reggie breathes a sigh of relief.

Reggie leaves his phone in his pocket for the remainder of the drive to Venice, joining the others in singing along to the music blaring through the speakers. He forgets about Caleb's texts until after they've made it onto the beach. He and Alex set up their towels while Luke immediately makes a break for the water, and Willie runs after him.

"You--" Alex groans. "He didn't put sunscreen on, did he?" he asks, turning to Reggie.

"Who, Luke?" Reggie makes a face. "Probably not."

"Idiot," Alex mutters as he rummages through his bag, grabbing his sunscreen before he takes off after the other two.

Reggie sits down on one of the towels, content to sit on the beach for a while. Even though they're in Southern California and it's a hot day, the ocean water is still a little too cold for his taste. He starts putting sunscreen on his arms, and then suddenly remembers the photos he promised Caleb.

It takes a little longer than he thought it would, especially since his hands are greasy from the sunscreen. He manages to snap a couple photos of the water, the sand, and even a nice panoramic view of the whole beach.

_These are lovely_ , Caleb replies and Reggie smiles. Before he can text back, another message comes through. _But where are you?_

For a second, Reggie is confused. He's at the beach… obviously. And then it clicks.

Caleb wants a photo of _him_.

He struggles to take a selfie, taking photo after photo and deleting one right after the other for a variety of reasons. The sun's in his eyes, he's making a weird face, the towel is rumpled. He's almost given up on the whole thing when Alex comes back and he jumps on the opportunity.

"Alex! Take a photo of me!" he tosses his phone to Alex, who gives him a weird look.

"Okay? Why?" Alex snickers softly. "Are you trying to become an Instagram model or something?"

"What? No," Reggie laughs uneasily. "Just take the photo."

"Okay, okay." Alex takes a couple photos and hands Reggie his phone back. "When did you get a new phone?"

"Uhh… yesterday," Reggie answers distractedly. He picks out one of the photos Alex took, deeming it good enough, and sends it off to Caleb. "I, umm, needed a new one."

"Yeah, I know." Alex laughs. "Your old phone sucked. But I thought you couldn't afford a new one?"

Reggie's phone buzzes and he looks down at the screen. _That's better. I like this view._

"Who are you texting?" Alex asks as he sits down next to Reggie, leaning over slightly to peer at the screen. Reggie snatches his phone away and clears his throat.

"Nobody."

"Dude," Alex says with a scoff. "Seriously. Everyone you know is here. Who are you texting?"

"I'm not texting anybody!" Reggie says, hiding his phone behind his back.

"What are you guys arguing about?" Willie asks as he and Luke approach them, both soaking wet.

"Nothing!"

"Reggie's texting someone secret."

"I--"

Luke grins widely. " _I_ know who he's texting."

"Who is it?" Alex asks, leaning forward with interest.

"It's--"

Reggie tackles Luke into the sand, and they get caught up in a wrestling match. Alex moves to break it up, but Willie stops him.

"They'll figure themselves out," he says as he pats his boyfriend's arm. "Let's just watch."

Alex rolls his eyes, pulling Willie down onto the towel he's sitting on and wrapping his arms around him. They both watch the other two wrestle until Luke eventually gets sand in his mouth and calls for a truce.

"Just tell them," Luke says as he spits out a mouthful of sand. "It's not a big deal."

"I--" Reggie groans. "It's just… a guy."

"A guy?" Alex repeats, and Willie whistles. "Wait, is this the guy you were so dressed up to meet the other day?"

Reggie groans again. "Maybe."

Willie whistles even louder and claps. "Nice!"

"Why didn't you just say that?" Alex asks.

"I don't know! It's new! I don't wanna jinx it." Reggie glares at Luke. "Happy?"

"Always," Luke says with a grin. He's definitely got sand in his teeth.

"I hate you," Reggie replies as he brushes sand out of his hair.

📸

As Reggie waits outside the security gate of his apartment complex, he wonders if his nerves before a date with Caleb are ever going to go away. He's not nervous, per se, but there's definitely something else mixed in with his excitement.

He wonders where Caleb's going to take him tonight. As per usual, all he was given was a time to expect the car to pick him up. Given the sorts of places that Caleb has taken him already Reggie can't help but expect it to be incredible.

The car arrives right on time, but when Reggie opens the door Caleb isn't in the backseat. He climbs in anyway and shuts the door behind him, feeling a little confused as the car pulls away from the curb. He pulls out his phone, intending to text Caleb, but then thinks better of it.

_Maybe he got caught up with work_ , Reggie thinks to himself. _He'll probably meet me wherever the car's going. There's no need to worry._

Reggie sighs as he puts his phone back in his pocket and turns his head towards the window. He spends the next forty minutes staring out the window, growing increasingly confused when the car goes from his apartment in the valley to the highway, not heading towards West Hollywood like Reggie originally expected.

When he sees the coastline, Reggie finally works up the courage to ask the driver just where he's driving to tonight. The driver glances in the rearview mirror and smiles at Reggie.

"Mr. Covington requested that you be brought to his residence tonight," he says.

Reggie stares at the driver for a few seconds. For a minute, he thinks he _has_ to have heard him wrong. There's no way Caleb would bring him to his house without telling him, right?

"I--" Reggie clears his throat. "His… residence?"

"Yes, sir." The driver nods. "In Malibu."

"Malibu?" Reggie nods. "Right. Of course."

"We'll be there soon," the driver says, and Reggie sits back in his seat.

If he wasn't nervous before, he definitely is now.

Reggie's in total awe of Caleb's house - or really, his _mansion_ \- from the moment the car pulls into the driveway. Although to be fair, Reggie would probably be impressed with a shack on the beach if it had the same view that Caleb does of the ocean. It's like nothing he's ever seen before, even with just having been at the beach a few days ago.

But Venice Beach is nothing compared to a _private_ beach in Malibu.

Reggie steps out of the car onto shaky legs as he looks up at the house. It's easily the nicest house he's ever seen, let alone about to set foot into. He half expects a butler to open the door, and he's relieved to see Caleb on the other side.

"Reggie," he says warmly as he steps aside to welcome him in. "I hope the drive wasn't too long."

"N-No," Reggie answers, tearing his eyes away from the sparkling entrance hall. He turns to look at Caleb and laughs awkwardly. "I, umm, wasn't expecting… this."

"I didn't mean to spring it on you," Caleb says with a chuckle as he leads Reggie through the house. "But I thought it might be nice for us to dine in, for once."

"You--" Reggie does a double-take as he enters Caleb's kitchen, which opens into the most spacious living room he's ever seen. The walls that face the ocean are made entirely of glass, giving them the _perfect_ view of the sunset. "You cook?"

"A little," Caleb says as he walks over to the stove. "I can get by, but my talents certainly lie elsewhere. Would you like something to drink?"

"Yeah," Reggie says, still looking around the room with awe. "I'll, umm, have whatever you're having."

Truth be told, Reggie's surprised when Caleb passes him a tall glass of… water. He looks at the glass and then up at Caleb, who seems a little embarrassed himself.

"I don't drink while I cook," he explains with a smile that's a little more bashful than Reggie's used to seeing on his face. "It's better if I keep my wits about me."

"Right," Reggie says, as though he has any idea what Caleb is talking about. The most cooking he does at home is usually ramen or mac and cheese. At best, he can make grilled cheese sandwiches, but at least one side usually ends up a little burned.

He takes the glass of water and turns back towards the room at large, but as badly as he wants to explore and look at every little thing, he stays put with his back against the kitchen island. This is Caleb's house, after all, and Reggie's a guest. He can't just go wandering off.

"You're welcome to look around, if you like."

Reggie turns his head to look at Caleb, who looks at him briefly as he carefully chops up some vegetables.

"Go ahead," he says, the confident smile that Reggie knows returning. "I don't mind."

Reggie laughs softly, his cheeks tinting with pink as he steps away from the kitchen island. He's still cautious with his steps as he walks further into the living room, keeping a firm grip on his glass. Even if it's just water, he still doesn't want to risk a spill.

The living room is decorated tastefully, a far cry from the sparse surroundings Reggie's used to in his own apartment. But the things he's drawn to the most is the art on the walls. There are a few paintings here and there, but most of it is photographs of varying sizes.

He knows very little about photography but he's always been fascinated by it. Split second moments of life captured forever on film mesmerize him, leading him to wonder what the day was like, what else was there that _wasn't_ caught by a camera?

Reggie's so caught up in looking at one photo in particular he doesn't even realize when Caleb comes to stand next to him. He's just suddenly _there_ , and Reggie startles so much that it's a miracle he doesn't end up dropping his glass.

"Sorry," Caleb says with a light chuckle. "I didn't mean to scare you."

"It's okay," Reggie says, laughing breathlessly as he presses a hand to his chest. "I just… didn't see you there."

"You like this one?" Caleb asks, pointing to the photograph Reggie was staring at.

"Yeah. It's…" He shakes his head, unable to find the words that could properly explain what he feels when he sees it. "It's amazing," he ends up saying, even though to his ears it sounds _totally lame_.

"Thank you," Caleb says. "It's one of mine."

"Y-Yours?" Reggie does a double-take. "You're a photographer?"

Caleb laughs. "I am."

"Wow. I mean…" Reggie looks around. "Like, is it a hobby, or--"

"It pays the bills," Caleb says modestly and Reggie can't help the laugh that escapes.

"I'll say! This house is amazing." He cringes at having used _amazing_ again so soon, but it's really not his fault. He's dealing with a lot right now, especially when Caleb's standing so close to him.

"Would you like a real tour?"

"Yeah! I mean… if you're not busy with…" Reggie gestures towards the kitchen and Caleb shakes his head.

"Everything's under control." He gently places his hand at the small of Reggie's back, easily guiding him out of the room.

By the time they sit down to dinner, Reggie's asked dozens of questions. He wants to hear all about Caleb's travels, his career, just _anything_ Caleb's willing to share. Reggie finds it all fascinating, and Caleb seems to find Reggie's interest in his life so charming that he's not bothered by it at all.

He wants to tell Reggie everything in a way he's never shared with anyone before.

"Wow," Reggie says, shaking his head after Caleb finishes a particularly detailed story about his last trip to Venice. "You've gone everywhere, haven't you? I haven't even been out of LA."

"You're young, there's still plenty of time." Caleb smiles warmly at him. "And there's plenty of art museums around the city that are just as impressive as The Guggenheim."

"Really?"

"Well," Caleb chuckles, "maybe not _just as_ , but impressive in their own right. There's The Getty, The Broad--" he cuts off after a moment as Reggie's eyes widen. "You've never been to those, have you?"

Reggie shakes his head, laughing bashfully. "Definitely not."

"Well," Caleb says as he picks up his glass of wine and swirls it around a little. "I'll have to remedy that sometime."

"I'd like that," Reggie replies, lifting his own glass up to clink it against Caleb's. It feels a lot like a promise.

📸

Caleb tries to insist that Reggie doesn't have to wash the dishes after they finish their meal, but he's adamant.

"You cooked! You shouldn't have to clean, too."

"I--" Caleb laughs. "Well, about that…"

Reggie stares at him for a moment before it clicks in his head. Caleb probably has people to clean up after him, if he wants it.

"Doesn't matter," he says, shaking his head as he takes Caleb's plate out of his hands. "I'm doing the dishes, and you can't stop me."

"Okay, okay." Caleb holds up his hands and Reggie smiles proudly.

He takes the dishes into the kitchen and places them next to the sink. After a minute or two of rummaging around in drawers and the cabinet under the sink, he finds some dishwashing gloves and the other supplies he needs.

"Umm, Caleb?" he says as he turns around, finding Caleb watching him with an amused smile. "I may need some help in figuring out where things go."

Caleb's smile grows. "Tell you what. You wash, I'll dry."

Reggie blushes. "Okay," he replies, ducking his head as he turns back to the sink. He fills half of it with hot, soapy water and starts on their plates as Caleb comes to stand next to him. He opens a drawer and produces a dishtowel, tossing it over his shoulder as he waits his turn.

Surprisingly, doing the dishes together feels completely normal. It's domestic, something that he does all the time back at home with Luke, but it's _different_. Reggie's certainly never felt his heart race from the brush of Luke's hand, anyway.

But every time it happens with Caleb, Reggie feels like he might faint.

It turns out that Reggie might've used a little bit too much soap, because the number of bubbles in the sink steadily grows as they work their way through the dishes. A few break off from the rest and float through the air, popping a few seconds later.

The next time it happens, Reggie finds himself blowing them around and popping them with his gloved fingers. When he realizes that Caleb is watching him, Reggie pauses.

"I--" His cheeks blush a deep red.

Caleb just smiles. A bubble floats close to him and he blows it right back towards Reggie. It goes right for his nose, popping the moment it touches his skin. Reggie starts laughing the moment it happens and Caleb joins in, the moment so ridiculous and so perfect that they can't help it.

And then, when the laughter fades away, Caleb kisses him.

Reggie freezes for a moment, his brain unable to do anything but have a minor freak out because _Caleb is kissing him!_ And just as he's about to reciprocate, Caleb suddenly pulls back.

"Sorry," he says, sounding like he's out of breath. "I… I didn't mean to-- if it's too fast, I--"

Reggie laughs, in spite of himself. He almost puts his hand up to his mouth, but then he quickly realizes he's still wearing the dishwashing gloves.

"No, I--" He quickly tears the gloves off and turns to face Caleb. "I mean, it's technically our fourth date, so… if you think about it, it's not fast at all."

The nervous look fades from Caleb's face as he smiles and sets down his towel. He turns towards Reggie, slowly reaching out to put a hand on Reggie's hip and pulling him a little closer.

"You sure?" he asks, looking down at Reggie's mouth for a moment.

"Yeah," Reggie whispers. He instinctively licks his lips as he looks up at Caleb. "You can kiss me again, if you want to."

Caleb puts his other hand on the side of Reggie's face, and Reggie's eyes immediately flutter shut. He can't even help it.

"Do you want me to?" Caleb asks softly.

"Yes," Reggie answers quickly, and before he can start to apologize for being so blunt, Caleb kisses him again.

**Notes for the Chapter:**

> catch ya next saturday <3


	5. Road Trippin'

**Notes for the Chapter:**

> officially halfway through the fic!!! exciting!!! hope you enjoy <3

It's been three weeks since Caleb first kissed Reggie. They've had a dozen dates since then, and most if not all have ended with Reggie being kissed within an inch of his life. He's not complaining by any means, because Caleb is a _great_ kisser. But he _is_ starting to wonder if they're going to move past kissing, since that's all they've done.

Every time Reggie thinks they might take the next step, Caleb pulls away. And Reggie's not sure if he can ask for more, so he just keeps his feelings to himself.

He does think about that first night at Caleb's house a lot, though. After that first kiss, they ended up on one of Caleb's expensive couches making out like a couple of horny teenagers. Hell, if Caleb had asked him to go further that night, Reggie probably would've said _hell yes_.

But he didn't, and he hasn't. And maybe that's normal, but it's kind of driving Reggie a little crazy.

It's getting harder to remind himself that Caleb's not his boyfriend. Ever since they started kissing it's become less and less of a job in Reggie's mind, and that's a slippery slope. It's not like he can _forget_ Caleb pays him, especially not when the money appears in his account every week. He's already paid off the rent _and_ all of the bills for the month, and for once he's actually got money left over. A _lot_ of money, actually.

Reggie knows he should save it. Up til now, he's never had a reason to have a savings account since his normal checking account was usually only barely above zero by the end of the month. But now he feels like he _should_ have a savings account. Even if it's for no other reason than to keep him from blowing his money on stupid shit.

That being said, even when he does blow his money, it's not even for _him_. After his first paycheck, he went with Luke to this weird music store that he's always talking about. He'd had his eye on this digital mixer - or something like that, Reggie really wasn't paying attention - for _months_ but six hundred dollars wasn't exactly spare change.

So, Reggie bought it for him. Luke tried to object, but it was half-hearted at best. He _really_ wanted it, after all, and Reggie was perfectly happy to spend his - or really, Caleb's - money on his best friend.

And it's not like he regrets doing it, because Luke isn't coming to him constantly with requests for other expensive equipment. Actually, Reggie's hardly seen Luke at all over the last three weeks, and it's not just because Reggie's been seeing a lot of Caleb.

It just seems like every time Reggie's coming home, Luke's on his way out. Reggie tries not to take it personally, because he knows that Luke is desperate to get his foot in the door at Capitol Records and any time he spends there is time well spent, but Reggie's having a hard time with the fact that it seems to be monopolizing _all_ of his best friend's time.

He just wants his friend back. He wants to sit on the couch and binge-watch dumb tv shows and share popcorn. Most of all, he really wants Luke's opinion on Caleb. He's one of the few people in Reggie's life who knows about Caleb and it's really starting to become a problem that he can't vent to anyone.

He can't even vent to Carrie, because they haven't been scheduled on the same shift in days. If Reggie doesn't talk to someone - and soon - there's a very good chance he may just implode.

The apartment is empty when Reggie leaves for his shift - something he's unfortunately gotten used to in the last few weeks. He's already feeling dismal about his upcoming shift at the restaurant as he shuffles his way across the courtyard, so wrapped up in his own thoughts that he almost doesn't notice he's passing by Julie until she says his name so loudly he jumps.

"Oh… hi!" he says, clearing his throat and trying not to feel too embarrassed.

"You okay?" Julie asks with a smile. "You looked a little spacey."

"Yeah, just…" He lets out a short breath. "A lot on my mind."

"Okay," she replies, nodding as if Reggie actually said anything helpful.

"It's just--" Reggie sighs. He doesn't have a _whole_ lot of time to spare, he really should be heading to the bus stop. But… he can't pass up an opportunity to vent, even if it's just a little. "Luke hasn't been home a whole lot and it's weird." He shakes his head. "I usually talk to him about stuff, you know?"

Julie gives him a sympathetic smile and pats his shoulder. "I know. He's your best friend, right?"

"Yeah," Reggie says, frowning a little. Maybe he's a bit more upset about Luke constantly ditching him than he thought. "I know he's working a lot but… it seems like there's something else."

"I'm sure he's just busy," Julie tells him as she pulls her hand back. "But, if I see him, I'll tell him you miss him, okay?"

Reggie flushes a little. "I-- you don't have to."

"He's your best friend," she repeats. "I'm sure he misses you too."

"Thanks, Julie." Reggie sighs. "I have to, umm…" he gestures towards the gate behind him and Julie's smile brightens.

"Right! Sorry. See you later!"

She spins around and takes off for her apartment, and Reggie continues on his way. Surprisingly, he feels a little better. And selfishly, he sort of hopes Julie _does_ run into Luke somehow and tells him to stop avoiding Reggie. He's not really sure if it'll work, since neither of them _really_ know Julie that well, but it's worth a shot.

📸

Carrie comes in for her shift about halfway through Reggie's, and when he sees her he nearly tackles her to the floor in a hug. She yelps in surprise but doesn't push him away, instead she wraps her arms around him and hugs him back. The look on her face when he pulls back is absolutely priceless.

"Are you… okay?" she asks.

"Yeah, sorry, I--" Reggie laughs a little and shakes his head. "I'm just really glad to see you."

"Aww," Carrie says as she puts her hand over her heart. "I missed you too."

She glances around, pulling Reggie off to the side to avoid being overheard by any of their coworkers or patrons. Reggie's confused at first, but he turns out to be grateful when he hears her question.

"I've been _dying_ to know, how's it going with Caleb??"

Reggie groans a little under his breath. He _really_ wants to tell her everything, but he knows he won't have the time to tell it all properly before he has to go back out onto the floor to check his tables.

"It's… really good." He sighs a little, already feeling sort of dreamy as he thinks about it. "Like, _really_ good."

Carrie raises an eyebrow. " _Really_?" she says with a short giggle.

"I--" Reggie groans again. "I have so much to tell you, but I have to go back out, and--"

"I know, I know. I have to clock in." Carrie pats his arm. "When you're off and I have a break, we're totally talking about this."

"Okay, yes," Reggie says, letting out a deep breath. "Thank god."

The last couple hours of Reggie's shift seem to drag on, and his head's a total blur. All he can think about is all the stuff he wants to share with Carrie. He wants her advice on his arrangement, he wants to ask if she's ever caught feelings for one of her clients - even though he's pretty sure he already knows the answer to that one, he just needs some encouragement that what he's feeling is normal, or at the very least, it's nothing to worry about.

By the time his shift actually ends, Reggie's practically vibrating out of his skin.

They end up in the alley behind the restaurant, which is usually where their coworkers who smoke go for their breaks. Carrie wrinkles her nose as she steps over several cigarette butts right outside the back door, but she doesn't complain.

"Okay," she says once the door's closed behind Reggie. "Tell me everything."

Reggie's mind suddenly goes blank. He chuckles nervously as she stares at him, waiting for him to unload on her like he was so eager to do earlier.

"I… umm…" He swallows hard. "I don't know where to start?"

Carrie laughs softly. "Okay, well, how about the dates? Have they been going well?"

"Oh, yeah," Reggie answers immediately. His cheeks turn a little pink and he ducks his head. "Actually, umm, we sort of… kissed?"

"You _sort of_ kissed?"

"Okay, well, like, he kissed me. Like, three weeks ago?" Reggie nervously scratches his neck. "He, umm, had me over to his house, and he made me dinner, and then--"

"Whoa, whoa," Carrie waves her hand a little. "Hold up. He made you dinner?"

"Y-Yeah?" Reggie's face falls. "Is that bad?"

"No," Carrie says, rolling her eyes. "It's sweet. None of my clients have ever done that."

"Really?" Reggie anxiously twists his fingers together. "Do you think it means anything?"

Carrie narrows her eyes. "Means anything? Like what?"

"I don't know, like…" Reggie splutters, "I don't really know what I'm doing so, like, I don't know if any of this is normal or if it _means_ something, and--"

"Reggie," Carrie says carefully as she takes one of his hands in her own. "Are you, like, falling in love with Caleb?"

"What? No!" Reggie laughs uncomfortably. "I… I just… no. Why would you say that?"

"I'm just--"

"It's not like I think about him all the time. And like, yeah the kissing is great but three weeks of just kissing is kind of starting to drive me nuts, but like I can't say anything because am I allowed to ask for more or is it just on his terms because he's the one paying me and like--"

"Reggie! Slow down." Carrie gives him a little shake. "Breathe."

She demonstrates, and he follows. Breathing in deeply and letting it out slowly, and his mind slowly stops racing.

"Sorry," he says sheepishly. "I just… I don't have anyone to talk to about this."

"Not even Luke?"

"No," Reggie shakes his head, "he's been gone a lot lately. I think he's just working a lot, but I dunno. And… he's never been in a real relationship so like, he's not exactly the best person to go to with this stuff."

"Reggie," Carrie says, in the sort of way that makes Reggie feel like he's said something wrong. "You do know this isn't a _real_ relationship, right?"

"I--" Reggie sighs softly. "Yeah, but…"

Carrie frowns. "I was afraid of this," she whispers softly.

"What? What do you mean??"

"I just--" Carrie sighs. "You're just… I don't mean this in, like, a bad way, but maybe you're just not cut out for this sort of thing?"

Reggie's face falls. "What do you mean?"

"I just mean that, like, you like Caleb. And that's great! I'm really glad you found someone that treats you well and everything, but this isn't a real relationship. He's not your boyfriend. You said it yourself, he's paying you."

"I know, but…" Reggie sighs heavily. "What, am I not allowed to like him?"

"No, that's not what I'm saying," Carrie says as she pulls Reggie into a hug. "I just don't want you to get hurt."

Reggie hugs her back tightly, shutting his eyes as he takes in a shaky breath. "What do I do?" he whispers.

"Maybe you should take some time away from Caleb for a little while," she says as she pulls back. "Like you would with a normal job, y'know?" She gives him a smile. "A work/life balance is important."

Reggie snorts. "Yeah, you're probably right."

"I really am glad he's treating you well," Carrie says after a few moments. "And that he's not a creep."

"He's really not," Reggie says with a sigh. "He's basically perfect. I don't even know why he's doing this when he could easily just have like, a normal boyfriend."

Carrie shrugs. "You'd have to ask him. But, in my experience, it's usually because it's less stressful this way. They don't have to worry about our emotions, like they would with a real partner."

Somehow, that doesn't make Reggie feel any better. He knows Carrie has a point - he probably should take some time to himself and have a break from Caleb. Maybe if he looked at his profile again, he'd have some other interested potential clients. Maybe if he started seeing someone else, he wouldn't be so attached to Caleb.

Just the thought of seeing someone else makes Reggie's heart sink. He doesn't _want_ to see anyone else. He just wants Caleb. And that's a big problem.

"You okay?" Carrie asks. Reggie lifts his head up, realizing he was stuck in his own thoughts for probably longer than socially acceptable.

"Yeah, I think so," Reggie answers, even though he feels the complete opposite. "Just a lot to think about, y'know?"

"Yeah." Carrie gives him a sympathetic smile. "Why don't you go home? Talk to Luke, if he's around."

Reggie snickers. "Yeah, maybe if I'm lucky I'll manage to catch him."

"Maybe you should text him," Carrie says as she starts heading for the door. "You know, actually _tell_ your best friend that you miss him. Couldn't hurt!"

"He'll just think I'm weird!"

"He's your best friend," Carrie repeats. "He already knows you're weird."

"That's… fair," Reggie mumbles.

Carrie grins at him as she pulls the door open. "See you around, Reg."

Reggie waves as she goes back into the restaurant. He takes a deep breath before starting his walk down the alley, heading for the street with the closest bus stop. He's got a lot to think about, and the bus ride home is the perfect place to start.

📸

When Reggie gets back to the apartment, it's still empty. It feels like an insult to injury, and Reggie goes into his room and gets right into his bed. He pulls the covers up and over his head while he presses his face into the pillow and lets out a deep sigh.

He feels stupid. He hates that he's upset over not seeing Luke, but he's even more annoyed by the fact that he's stressing himself out over Caleb for no reason.

It shouldn't be this difficult. He knew what he was getting himself into. They have a contract, for god's sake. Reggie knew going in that this was a business arrangement, and he had to go and mess it up by catching feelings.

He feels pathetic. Like he's no better than a child. He should've known better, he should've known that he wouldn't be able to handle something like this.

Reggie rolls onto his back and takes a deep breath, scrubbing his hands over his face before he pulls his phone out of his pocket. He's going to text Caleb and tell him that he needs a break. Maybe just a week would help.

He opens a new message, but can't find it in him to type anything. As he stares at the screen, a typing bubble pops up on Caleb's side of the conversation and Reggie sits bolt upright in bed. He waits patiently for the little bubble to disappear, and a message replaces it a few seconds later.

_Are you available to talk?_

Reggie swallows. Maybe Caleb's feeling the same thing he is. Maybe this is him asking for some time apart, so Reggie doesn't have to be the bad guy.

_Yeah, I just got home from work,_ he replies. A few seconds later, his phone is ringing.

"Hello?" he answers shakily, even though he knows full well who's at the other end.

"Hi," Caleb replies. "I'm not disturbing you, am I?"

"No, no," Reggie says as he runs his hand along the top of his comforter. "I was just…" He clears his throat, thinking better of telling Caleb that he's in bed. "What's up?"

"I'm calling because I wanted to talk to you about this weekend." Caleb pauses for a moment and Reggie holds his breath. "I know we were supposed to have our date, but something's come up. I have to go out of town."

"O-Oh?" Reggie exhales sharply. "I… okay? That's--"

"I tried to get out of it, but…" Caleb chuckles. "I'm afraid I have no choice."

"That's okay," Reggie says, starting to feel a little relieved. "I totally get it."

"I'm glad to hear that. I was a little worried you might be disappointed."

"No, I…" Reggie pauses for a second. "It's okay, I understand. You've got, like, responsibilities and stuff."

"I appreciate that." Caleb hums softly. "But, I did have an idea."

"An idea?"

"Would you like to come with me?"

"I--" Reggie's brain stops working. "W-With you?"

"Yes."

"I… wh-where?"

"New York. Just for the weekend." Caleb goes on to explain that he apparently promised to make an appearance at a gallery opening for an associate of his, which he doesn't actually remember doing but it's supposedly too late to say no. Reggie, however, hears exactly none of this because he's too busy internally freaking out.

This is not what he expected. This is the opposite of what he was trying to do. He was going to ask Caleb for space, and now he's being asked to go to New York with him?!

What surprises Reggie even more is the fact that even though he's reeling from being asked, somehow the only thing he can manage to say in response is _yes_.

"Really?" Caleb asks.

"Yes," Reggie repeats. "I'd love to go to New York with you."

Caleb laughs softly and Reggie can _hear_ the smile in his voice. It does things to his heart that he half-wishes it didn't, but he can't stop himself from smiling either.

"Excellent," Caleb says. "I'll make all the arrangements, you don't have to worry about a thing."

"Okay," Reggie replies, feeling a little giddy. "Just let me know where to go, and I'll be there."

"I will." Caleb pauses for a moment, and Reggie almost thinks he's hung up. "I, umm, I'm glad you agreed to come with me."

Reggie's entire body flushes. "M-Me too."

They say their goodbyes and the moment the line goes dead, Reggie collapses onto his bed and squeals into his pillow like a preteen girl. It's super embarrassing, and for once he's glad he's alone in the apartment.

After he's composed himself, he unlocks his phone again and starts a new text to Luke. Carrie was right, he needs to be more open with his best friend.

_RED ALERT SOS CALEB IS TAKING ME TO NYC FOR THE WEEKEND WHERE THE FUCK ARE YOU COME HOME I NEED TO TALK ABOUT THIS!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!_

Surprisingly, Luke responds in less than a minute.

_??????????????????? WHAT THE FUCK DUDE HOW WHEN WHY_

_WHEN ARE YOU COMING HOME???_ Reggie texts back, groaning and grumbling at his phone as Luke types his response.

_omfg CHILL ik i haven't been home but dw tonight its u and me bro love u_

"I hate you," Reggie says as he types back _love you too dick_. He tosses his phone aside and lays back down, closing his eyes as he lets out a deep breath.

This is probably a bad idea. But he's only human. He's allowed to make mistakes once in a while.

**Notes for the Chapter:**

> see you next week :)


	6. The Sweet Escape

**Notes for the Chapter:**

> AHH VERY EXCITING THINGS HAPPENING IN THIS CHAPTER!!! a lot of _firsts_... if you know what i mean...

Luke said he'd be right back ten minutes ago. Reggie's been watching the time on his phone since Luke went out the door and he's starting to get anxious. If he doesn't leave soon, he's going to be late meeting Caleb.

Maybe he should've accepted the offer of being picked up, but Luke insisted on being the one to drop Reggie off. He'd been trying to make more time for Reggie the last few days, and while Reggie really appreciated it, this wasn't the _best_ time. At this rate he'll have to call an Uber and bribe the driver to go way over the speed limit.

He's going to give Luke five more minutes. If he's not back by then, Reggie's calling an Uber.

With just one minute to spare, Luke bursts through the door with a set of keys in one hand and a triumphant smile on his face.

"Come on!" he shouts as he grabs Reggie's bag. "Don't wanna be late!"

Reggie wordlessly follows Luke out of their apartment, feeling very confused indeed when Luke leads him out to the parking lot and over to Alex's car.

"Uhh…" Reggie laughs incredulously as Luke pops the trunk and puts the bag inside. "Alex is letting you use his car?"

" _Us_ ," Luke corrects as he slams the lid of the trunk down.

"Okay, _us_ ," Reggie says as he opens the passenger door. "How'd you manage that?"

"Let's, uhh, not talk about it, okay?" Luke says as he slides into the driver's seat and puts the key into the ignition.

"You owe him big, don't you?" Reggie chuckles as he puts his seatbelt on.

"Shh," Luke says, batting at Reggie's face as he starts reversing the car out of its parking spot. "I don't wanna hear your voice unless it's reading me directions off your fancy phone."

Reggie rolls his eyes as he pulls up his text thread with Caleb, copying the address of the Van Nuys Airport. Neither of them have ever been to this particular airport - but at least Luke has one up on Reggie by having been to _any_ airport before. Reggie's never been on a plane, and so he has absolutely no idea what to expect other than what he's seen in movies and on TV.

He passes along Caleb's instructions once they get closer, and Luke whistles when they get to drive through the fence and head towards the tarmac.

"So fancy," he teases. Reggie snorts and punches Luke's shoulder, but deep down he's freaking out.

This is _huge_ , not just because it's the first time he's leaving LA or getting on a plane, but for his and Caleb's relationship. He has no idea what could be in store this weekend, and the closer he gets to the plane the more nervous he gets.

_It'll be okay_ , he tells himself. _Just think of it like a business trip_. _A business trip between two colleagues who… sometimes kiss. It won't be weird unless you make it weird._

Luke slows the car down and parks it where he's guided to by some official looking guys, and both of them stare at the private jet in front of them.

"Damn," Luke says with another impressed whistle.

"Yeah," Reggie says weakly. "This is a good idea, right?" he asks, turning away from the windshield and towards Luke.

"Hell yeah, dude!" Luke claps his shoulder. "Free trip to NYC!"

Reggie laughs nervously, and they both get out of the car. Luke pops the trunk and as Reggie gets his bag, he hears Luke clear his throat.

"Is that him?"

Reggie looks up and sees Caleb at the foot of the stairs leading up to the door into the plane. He looks as stylish as ever and it makes Reggie a little weak in the knees.

"Yeah," he answers, taking a deep breath as he closes the trunk.

"Nice," Luke clicks his tongue in approval. "Okay," he says, putting his hands on Reggie's shoulders. "You'll text me when you land, right?"

"Yeah," Reggie says with a sharp exhale. "And when we get to the hotel."

"Good," Luke says as he pats Reggie's shoulders. "Just… keep in touch, okay?"

"I will," Reggie promises. "Don't worry."

Luke smiles at him and then pulls Reggie into a tight hug. Reggie grunts a little from the force of it, but he hugs Luke back.

"Be safe," Luke murmurs before he pulls back. "And have fun!"

"Okay, Reggie replies with another sharp breath. "Here I go."

"You've got this!" Luke assures him, and Reggie laughs.

"I hope so!" he says, squeezing Luke's hand once more before he starts walking towards Caleb. He's smiling when Reggie meets him, but his sunglasses hide his eyes.

"I was beginning to worry about you," Caleb says as he presses his hand to the curve of Reggie's cheek. Normally he'd probably kiss Reggie hello, but since he's pretty sure Luke is still watching, he's a bit relieved that Caleb doesn't.

"Sorry," Reggie says with a nervous laugh. "We had to borrow our friend Alex's car--" He turns around and waves at Luke, "--and it, uhh, took a little longer than I thought it would."

"It's alright," Caleb says as he slips his arm around Reggie's waist and leads him to the stairs. "You're here now, and that's what matters."

Reggie flushes as he starts climbing the stairs, gripping the rails a little harder than necessary to try and stop his hands from shaking so much.

The inside of the plane looks even better than Reggie imagined. Granted, all he had for reference were maybe a few movies and a handful of music videos with private planes, but it's so different to see it in real life.

Caleb has to guide him to a seat by a window because Reggie freezes, almost afraid to touch anything. A woman appears from the back of the plane and takes Reggie's bag, asking if she can get him something to drink. Reggie looks at Caleb, who smiles at him.

"Anything you like," he tells Reggie, which isn't entirely helpful for Reggie's poor racing mind.

"Uhh… a Coke?" he answers finally, and the woman nods at him before turning to Caleb and asking if he'd like his usual. Reggie stares wide-eyed as Caleb replies in the affirmative and thanks her.

"Is this your first time on a plane?" Caleb asks and Reggie laughs nervously.

"Yeah, I've never really been anywhere. Not even out of LA, really."

"Not once?" Reggie shakes his head. "Well, then I'm honored to be accompanying you on your first trip."

Reggie snorts. "Isn't it the other way around?" he asks, and Caleb grins.

"I suppose you're right."

The woman comes back with their drinks a moment later, and Caleb raises his glass.

"To your first plane ride," he says. Reggie blushes as he clinks his glass against Caleb's, watching him wince a little as he swallows.

"What are you drinking?" he asks curious as he taps his fingers against his glass. Caleb swirls his drink around and chuckles.

"Liquid courage," he says as he takes another sip. "I'm not _overly_ fond of flying, myself."

"Oh." Reggie nods, suddenly feeling more nervous than before.

Caleb gets up from his seat and takes the one right next to Reggie, buckling his seat belt and smiling when Reggie gives him a confused look.

"This is your first flight," he says as he extends his hand to Reggie. "In case you need it."

Reggie's cheeks blush a darker shade of pink, and he jumps when the door to the plane suddenly slams shut.

"Do I have to wait for take-off?" Reggie asks, sighing in relief when Caleb shakes his head. "Good," he says as he grabs Caleb's hand and laces their fingers together.

He takes another sip of his Coke to calm his nerves while Caleb finishes his drink and hands the glass to the woman as she passes by. Reggie eventually hands his over as well when the plane starts to move, and he presses his back against his seat and tries to take a deep breath.

Through the window, he watches the world start to go by and his heart races, his hand tightening around Caleb's. His stomach jumps as the plane picks up speed and he shuts his eyes when it starts to lift into the air. Suddenly, Reggie feels Caleb's other hand against his cheek and when he opens his eyes, Caleb is leaning across his seat towards him.

"It's okay," he tells Reggie in a soft, calm voice. "Just breathe."

"O-Okay," Reggie answers shakily as he tries to take in a normal breath. Caleb smiles and rubs his thumb against Reggie's cheek, and then he leans in to kiss him.

It instantly relaxes Reggie, so much that he feels a little dazed when Caleb pulls back.

"Forgot to do that earlier," Caleb tells him, and Reggie laughs.

"You can do it again," he says, shifting around in his seat to face Caleb properly, "if you want to make up for it."

Caleb grins widely and does just that.

📸

Once the plane levels off, Reggie doesn't feel as nervous as he did before. He stares out of the window, marveling at the clouds as they pass by. He takes a dozen or so pictures on his phone out of his own window, and then he slips out of his seat and past Caleb to switch to another window on the other side of the plane.

Caleb watches him with amusement, and Reggie's so swept up with his own excitement that he completely forgets to be embarrassed about it. When he finally tears his eyes away from the world outside, Reggie finds a small feast set up in front of Caleb and his original seat. Caleb beckons him over and Reggie quickly scrambles to join him.

"I think I like flying," he says as he reaches for one of the sandwiches, and Caleb laughs.

"Flying does have its perks," he says.

"So…" Reggie pauses to swallow his bite, "is this like, _your_ private plane… or--"

"In a manner of speaking," Caleb answers. "It's shared between myself and a few colleagues - and we split the costs." he chuckles as he serves himself some food. "Private planes are expensive, even for the wealthy."

Reggie glances around and even the astronomical number his brain comes up with seems too small. "I don't think I wanna know," he decides a few seconds later.

Caleb snorts, popping a chip in his mouth. "I think that's probably wise."

They make casual conversation as they eat, mostly made up of Reggie asking about all the places Caleb's been on the plane. He's fascinated to discover that the seats turn into beds, and he flushes a deep red when his brain makes a simple connection, given his present company.

Thankfully, despite the obvious change in color of Reggie's face, Caleb doesn't comment on it. Instead, he turns the conversation in a direction Reggie didn't expect.

"That charming man who dropped you off--" he says, calm and collected. "--you said his name was… Alex?"

"Oh, no--" Reggie answers, totally oblivious, "--that was Alex's car, but it was Luke who dropped me off."

"Luke," Caleb repeats.

"Yeah, he's my best friend," Reggie goes on. "We live together. Alex and his boyfriend live in the apartment next to ours…" he rambles on for another few minutes about what he thinks Luke probably had to promise Alex in order to get his keys. Reggie doesn't notice the way Caleb stiffens a little every time he mentions Luke's name.

"It sounds like your friend group is made up of quite the cast of characters," Caleb says with mild amusement. Reggie blushes, finally realizing that he was totally rambling.

"Yeah," he says softly. "They're kinda weird, but--" he shrugs, "--so am I, so we all get along."

Caleb chuckles warmly. "An important quality," he says. "Everyone's weird in their own way."

Reggie rolls his eyes without meaning to. "Sorry, I just…" he laughs nervously. "I just picture your friends as like, fancy and smart and mature."

Caleb hums, considering the idea. "You'll meet some of them tonight, you can assess them yourself and let me know what you think."

"I…" Reggie gulps. "I'm gonna meet your friends?"

"Well, a few." Caleb sighs and chuckles under his breath. "Trevor will likely be flighty at best. He's the one who owns the gallery and bullied me into coming in the first place."

Reggie laughs. "Is he an artist?"

"No," Caleb answers with a laugh, "but he insists he has an eye for art. I'm not sure what the opening will consist of, so just… be prepared."

Reggie shrugs. "Whatever it is, I'm sure it'll be cool." Caleb shakes his head and smiles.

"Your optimism is… endearing."

Reggie swallows, ducking his head as he blushes. Caleb leans over and tucks his hand under Reggie's chin, tilting his mouth up so he can kiss him. Reggie moans softly into Caleb's mouth, shivering when he pulls away. Caleb clears his throat and chuckles.

"I'm going to have to keep an eye on you tonight," he says softly as he takes Reggie's hand. Reggie looks down as their fingers interlock and he blushes again.

"How come?" he asks.

"If I don't, someone might try and steal you away." Caleb looks at him and smiles. "You're very… desirable."

Reggie snorts, his face turning an even darker shade of pink. "I don't know about that," he mumbles. Caleb brings Reggie's hand up to his mouth and brushes his lips against the knuckles.

"Believe me," he says, his bottom lip dragging across Reggie's skin as he speaks. He could've asked anything of Reggie in that moment, and he would've said yes without a moment's hesitation.

Reggie clears his throat and takes a shaky breath, reminding himself that they're not alone on the plane, and besides, Caleb probably wouldn't want to join the Mile High Club in a plane he shares with other people. _Business trip_ , he reminds himself firmly. He takes another breath, deeper this time, and settles back into his seat, keeping a tight grip on Caleb's hand.

📸

Once the plane lands, the rest of the day passes by in a blur. They're whisked away from the airport in a town car and head into Manhattan, and Reggie's eyes are practically glued to the window. The traffic rivals Los Angeles, he thinks, but the streets are _so much smaller_. Everything seems so packed together and every single building seems like it's thousands of feet high.

Reggie continues staring at his surroundings when they reach the hotel, feeling overwhelmingly like a tourist as Caleb leads him into the lobby and heads for the front desk. Within just a few minutes, they're in the elevator heading to the upper floors.

Truth be told, Reggie probably should've expected that Caleb would rent a penthouse suite, but it likely wouldn't have been any less spectacular to see if he'd been expecting it. Caleb discusses a few things with the bellboy as Reggie explores the main part of the suite, spending most of the time staring out the giant windows at the view of the city. It's a little nerve wracking, looking down from that height, but Reggie can't stop marveling.

He snaps a couple of photos, sending them to Luke along with a message that they made it to the hotel safely. Luke's reply comes through a few seconds later, but Reggie's attention is stolen by Caleb calling his name.

"I have something for you," he says as he gestures for Reggie to come to him.

"What?" Reggie asks as he crosses the room, and Caleb steps aside to reveal several large boxes. "These are… for me?"

Caleb nods. "I took it upon myself to get you an outfit for tonight. I hope that's alright."

"I mean… yeah?" Reggie laughs as he carefully opens the first box. By the time they're all open, he has a full suit and a shiny new pair of shoes. "Caleb… this is too much," he says softly.

"Nonsense," Caleb says as he presses a kiss to Reggie's temple. "I think it's just enough."

Reggie flushes. "If you say so." He's never owned a suit in his life. He wouldn't even know where to wear one.

Caleb shows him into the bedroom with an attached ensuite bathroom so he can get cleaned up and dressed for the gallery opening. Reggie takes a quick shower before he puts on the suit, treating every piece like it's made of glass. It's by far the most expensive thing he's ever worn and it fits him perfectly.

When he makes his way back out into the main room, Caleb's nowhere to be found. Reggie assumes he's getting ready and goes to sit down, but then thinks better of it. He doesn't want to mess up his new clothes. Instead he stays standing and finally remembers to answer Luke's text.

_DUDE WTF WHERE ARE YOU_

Reggie laughs as he types back _penthouse suite!!!!!! crazy!!!!!_ , and then he opens his camera and snaps a quick selfie of his new outfit. _Check out what caleb bought meeee!_

They reply back and forth for a while, until Caleb finally reappears. As soon as Reggie sees him, he forgets all about texting Luke. Caleb looks even better than he did at the airport this morning, and Reggie has to actively stop himself from drooling.

"You look…" Caleb says as he admires Reggie in his new suit. Reggie can't even form words to express what he's feeling. "Perfect."

"I…" he laughs bashfully and waves his hand. "No, you--" he tries clearing his throat, but it doesn't help him to gather his thoughts well enough to actually say something.

Caleb grins. He doesn't seem to care one bit.

"Shall we?" he asks as he holds out his hand. Reggie nods and takes it.

To someone like Caleb, the gallery opening is an evening full of glad-handing and pretending to care about what other people are talking about. But to Reggie, it's a whole new experience. He sticks close to Caleb and keeps quiet, half-expecting to be forgotten about in conversation. To his surprise, every time Caleb greets someone new he introduces Reggie as his _date_.

The little voice in the back of Reggie's head that keeps reminding him that this is a _business trip_ gets softer and softer with every passing hour.

It's probably aided by the fact that there's complimentary champagne absolutely everywhere, and Reggie's not about to turn it down. At the very least, it gives him something to occupy his hands when he's not clutching Caleb's arm. And it's also a nice distraction for his mouth when he has nothing interesting to say (which, if he's being honest, happens a lot more often than not).

Caleb stays true to his word and keeps Reggie close to him throughout the night, and while he thinks most of the people they meet seem nice enough, there are definitely a few that Reggie totally gets a weird vibe from. Their eyes study him a little too closely, their smiles are a little too sharp. It's a relief when Caleb pulls him away and Reggie doesn't have to be around them anymore.

He's only left alone once. Caleb excuses himself to use the restroom and Reggie stays right where he is, standing in front of one of the largest paintings in the whole of the gallery. While he doesn't really understand modern art, he likes the look of it. The colors are subdued but still remain eye-catching, and the minutes pass by like seconds as he studies it.

In fact, he's so wrapped up in looking at it that he doesn't even realize when Caleb comes back. As far as Reggie's concerned, he just suddenly appears next to him.

"See something you like?" Caleb asks, and Reggie startles with a surprised giggle.

"I-- yes," he says, turning to face Caleb. "Absolutely."

Caleb laughs and Reggie blushes. They both know he wasn't talking about the painting, but Reggie didn't _mean_ to say it aloud.

"I think it's time to get you back to the hotel," Caleb says, dropping his voice as he carefully takes the empty champagne flute out of Reggie's hand and puts his hand at the small of Reggie's back.

"Okay," Reggie answers, feeling a little light-headed. He guesses it's probably from the champagne, but it's probably not helping that Caleb is _so close_ to him that he can smell the cologne on his skin.

As they wait at the entrance for a car to pick them up, he leans into Caleb and inhales, trying to commit the scent to memory. Caleb curls his hand around Reggie's hip, pulling him closer. Reggie's hand twitches at his side, and for a moment he fantasizes about putting his hand on Caleb's chest and tilting his head up to ask for a kiss. If they were really dating, he could just do it. He wouldn't even hesitate.

Reggie puts his hand in his pocket and closes his eyes as he takes a deep breath. The car pulls up a few seconds later, and he climbs into the backseat with Caleb right behind. He absolutely doesn't mean to, but Reggie ends up falling asleep before they make it back to the hotel.

📸

Reggie wakes up a little disoriented the next morning. He's got a bit of a headache from too much champagne and not enough food the night before, and it takes a couple seconds for him to remember where he is. He's embarrassed when he realizes the last thing he remembers from the night before is getting into the car to come back to the hotel, which means Caleb likely had to carry him in and… from the looks of it, he changed Reggie's clothes too.

Because he definitely didn't sleep in his suit. Caleb must've gone through Reggie's bag to find his pajamas, which is even more embarrassing.

Reggie groans softly as he puts his head in his hands, sighing as he glances around the room. The other side of the bed was clearly slept in, and Reggie's cheeks turn red as he groans again. Does this mean that he and Caleb actually slept in the same bed last night and he _missed it_?

"Stupid, stupid, _stupid_!" he mumbles to himself as he smacks himself in the forehead before pulling himself out of bed. For all he knows, he's already running late.

Reggie has no idea what the plan is for the rest of the weekend. They could very well be flying back to LA today.

He ventures out into the main room with a sheepish shuffle, and finds Caleb sitting at the table. He looks up when Reggie comes towards him and smiles widely.

"Sleep well?" he asks.

"Y-Yeah," Reggie replies shyly. "Sorry for falling asleep in the car," he says awkwardly, "I, umm, didn't realize I was so tired."

"Don't worry about it," Caleb tells him as he gestures to the table full of food. "Please, join me."

Reggie nods and takes the seat across from him, helping himself to one of the bagels and a few strips of bacon. Caleb takes a sip from his coffee cup and offers to pour some for Reggie, who happily accepts.

"So," Caleb says a few minutes later, "I was thinking, since it's your first time in New York, we should do what _you'd_ like to do."

Reggie pauses mid-bite. "You mean…" he takes the bagel out of his mouth and swallows, "...we're not going back to LA today?"

"No," Caleb replies with a laugh, "of course not! What sort of first trip would that be?" He shakes his head. "We should make it special."

Reggie swallows hard. "Okay," he answers with a nervous laugh. "I, umm… we should go to, like, Central Park?"

"Okay," Caleb says with a nod. "What else?"

"Umm… the Statue of Liberty?"

"Alright," Caleb chuckles.

"And… Times Square?"

"Of course. Anything else?"

"What about… a Broadway show?" Reggie asks hopefully. If this is his only chance to come to New York, he should probably take advantage of it.

"Any show in particular?" Caleb asks and Reggie hums.

"I, uhh, don't even know what's, like, playing?"

Caleb chuckles and winks at him. "We'll figure it out, don't worry."

"Okay," Reggie replies, smiling widely as he picks his bagel up and takes a bite. He makes sure to chew it normally and try not to stuff his face, even though he's so excited about the prospect of the day ahead of them that part of him wants to forego breakfast entirely.

Their day out in New York City is a total whirlwind. Reggie takes hundreds of photos at every single destination, so much that Caleb teases that he'll be out of a job if Reggie keeps up like this. Reggie flushes, knowing Caleb's just kidding, but it warms his heart that he feels comfortable enough to tease him like that.

As the day winds on, Caleb fulfills every single one of Reggie's whims, and even adds in a few things he didn't think of. He takes Reggie to Fifth Avenue and they wander around Tiffany & Co. just because, and it feels like they're in a movie. When Reggie stares too long at a pendant necklace, Caleb buys it without a second thought. Reggie tries to tell him that he doesn't have to, that just because he was looking at it doesn't mean he has to have it, but Caleb insists.

"Think of it like a souvenir," Caleb tells him as he hands over the signature blue box. Reggie bites his bottom lip, holding back his smile as he takes the box. When they ride back down to the first floor in the elevator, he presses a kiss to Caleb's cheek.

"Thank you," he says when Caleb turns to look at him. "You didn't have to, but thank you."

The bow of Caleb's cheek is tinged with pink when he tells Reggie he's welcome, and when the elevator doors open he takes Reggie's hand and doesn't let go.

In the evening, they go to a performance of Hamilton and top it off with a late-night dinner at one of Caleb's favorite restaurants. Unlike the night before, Reggie is brimming with energy when they get back to the hotel. He can't stop talking about all the incredible things they did that day, and Caleb listens with fond amusement.

Reggie's sitting on the foot of the bed as Caleb starts getting ready for bed, still talking a mile a minute about how impressed he was with the performers in Hamilton. It's not until Caleb removes his belt that Reggie realizes that Caleb's getting undressed, and suddenly he drops his eyes to the floor and his cheeks turn pink.

"I, umm, I'll be right back," he says as he goes into the ensuite and quickly shuts the door. He looks at himself in the mirror and takes a deep breath.

He may have missed it the night before, but not tonight. They're going to share the bed and Reggie has to get a grip on himself. He can do this, he can be normal about this.

As he starts taking his own clothes off, he keeps repeating _you can do this_ to himself. If he says it enough times, he might actually start to believe it. He splashes a little cold water on his face before he goes back out into the bedroom, and finds Caleb sitting up in the bed with a book on his lap.

Reggie swallows hard as he looks at him. Caleb's not wearing a shirt, and it's the first time Reggie's actually seen him without one. He lets himself look a little too long, ending up being caught staring by Caleb. He smiles and pats the open spot in the bed beside him, and Reggie lets out a nervous laugh as he sets his clothes down and crosses the room.

He only mildly regrets his choice to wear just boxers to bed when he climbs under the covers. If he's not careful, this might be a little harder than he thought it would be.

"Tired?" Caleb asks.

"Y-Yeah," Reggie answers, even though his mind and body are so wired that sleep seems like an impossibility.

"Okay," he says quietly as he sets his book aside and clicks the bedside lamp off. The room plunges into darkness save for the ambient light coming in through the window. "Good night," he tells Reggie as he leans over and gives him a good night kiss.

Reggie moans softly into Caleb's mouth and cups the back of his head, keeping him there for a little longer than necessary. Caleb shifts, moving closer to Reggie as his hand tightens in the sheets next to him.

"Reggie," he says breathlessly as he pulls back. "I--"

"I'm not tired," Reggie says quickly. His eyes haven't fully adjusted to the dark yet, but he can still see the curve of Caleb's smile.

"No?" he says as he gently rubs his nose against Reggie's. He kisses him again, sighing as he puts his hand on Reggie's waist. "Neither am I," he admits.

"Can we--" Reggie swallows hard and slowly brings his other hand up and puts it on Caleb's shoulder. "I know we haven't talked about it, but--"

"Do you want to?" Caleb asks in a low voice.

"Yeah," Reggie breathes out in a rush as he nods his head. "Please."

Caleb grunts softly and leans down for another kiss, and this time Reggie doesn't hold back. He kisses Caleb with everything he's been building up over the last month. He wants whatever Caleb is willing to give him and he _desperately_ wants to give him whatever he wants in return.

The kiss deepens and Caleb's hand at Reggie's waist tightens its grip as he presses his body flush against Reggie's. It sends sparks shooting across Reggie's skin, especially when Caleb slips his leg - covered in silky smooth pajamas - between Reggie's and rolls his hips down.

Reggie moans and reciprocates the motion, rocking his hips up into Caleb as he gets hard. It's not the first time he's gotten hard while kissing Caleb, but it's definitely the first time that Caleb's actually done something about it. He drags his hand down from Reggie's hips and places it firmly on top of his cock, pressing down against the fabric of his boxers and squeezing.

"Fuck," Reggie moans, breaking the kiss to breathe hotly into the crook of Caleb's neck. Caleb gasps in his ear as he ruts against Reggie, shoving his hand past the elastic of his waistband to get his hand around Reggie's cock properly.

Digging his fingers into Caleb's shoulders, Reggie throws his head back and moans loudly as Caleb attaches his mouth to the base of his throat and sucks. It's overwhelming and perfect and all Reggie can do is want more.

And then Caleb starts trailing a line of kisses down his chest, shuffling down in the bed until he's hovering over Reggie's hips and pulling his boxers down over his thighs. Reggie scrambles to hold onto something, _anything_ , and twists his hands in the sheets below him as Caleb takes the head of his cock into his mouth for the first time.

" _Caleb_ \--" Reggie chokes out, shivering with his whole body as Caleb sucks him. This is absolutely not how he pictured this going, but he's _absolutely_ not complaining. Caleb's mouth is unlike anything he's ever felt before and in that moment, it's everything he could ever want.

Reggie's too overwhelmed to even be embarrassed by how quickly his body responds to Caleb's touch. Everything is amplified a hundred times over and Reggie shouts Caleb's name as he comes, his breaths coming hot and heavy as he shudders through it.

Caleb crawls back up his body and Reggie wastes no time at all to bring their mouths back together. He slips his hand down between them and into Caleb's pajamas, finally getting his hand around Caleb's cock. It's hot, thick, and long in his hand and _god_ _why didn't they do this sooner_?

"Do you--" he tries to ask, but Caleb clutches his face and refuses to let go.

"Kiss me," he begs. Reggie can't say no to that.

He keeps kissing Caleb as he touches him, pulling out every trick he's ever used on himself to get Caleb off. The air around them is heavy and filled with moans, and by the time Caleb comes it feels like hours have passed since they started kissing.

Reggie isn't sure how he ever lived without knowing what Caleb sounds like when he comes. And now that he knows, he might be addicted to it. All he can think about is finding out all the different ways he can make Caleb sound _like that_ , and how they've got nothing but time.

Caleb sighs in satisfaction as he rolls onto his back, and Reggie curls up against him. His hand is still around Caleb's cock, but neither of them really seem to mind. If Reggie said he wasn't thinking about trying to get him hard again, he'd be lying.

"Reggie," he whispers, turning his head towards him and brushing the hair out of Reggie's face. He cups Reggie's cheek with his hand and kisses him sweetly, rubbing his thumb against the bow of his cheek as he hums softly. "You're perfect."

Even in the darkness, Reggie's certain that Caleb can see the blush in his cheeks. He's so far gone and in the moment, he doesn't even care.

**Notes for the Chapter:**

> see you next weekend!

**Author's Note:**

> [here's the playlist i made for the fic](https://open.spotify.com/playlist/0bwLPt33Y8AU7tdhPVtGOb?si=z5BDr4CnTKSHupmrAIG7Uw) and [this is my tumblr](https://astorytotellyourfriends.tumblr.com/)


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